People Ops: Lessons in Culture and

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People Ops
Lessons in Culture and
Leadership From Building Startups
―
Patrick Caldwell
 People Ops
Lessons in Culture and
Leadership From Building
Startups

Patrick Caldwell
People Ops: Lessons in Culture and Leadership From Building Startups
Patrick Caldwell
London, UK

ISBN-13 (pbk): 978-1-4842-9818-3 ISBN-13 (electronic): 978-1-4842-9819-0

https://doi.org/10.1007/978-1-4842-9819-0

Copyright © 2023 by Patrick Caldwell

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Table of Contents
About the Author��������������������������������������������������������������������������������vii

Preface������������������������������������������������������������������������������������������������ix

Chapter 1: Building from Scratch���������������������������������������������������������1

Ground Your Decision-Making�������������������������������������������������������������������������������3
Simple Is Sexy�������������������������������������������������������������������������������������������������������5
Done > Perfect������������������������������������������������������������������������������������������������������6
Self-Service FTW��������������������������������������������������������������������������������������������������8
Decision by Committee Sucks����������������������������������������������������������������������������10
Beware the Magpies�������������������������������������������������������������������������������������������12
Your People Strategy Is Your Business Strategy�������������������������������������������������14
Summary������������������������������������������������������������������������������������������������������������15

Chapter 2: Leadership������������������������������������������������������������������������17
Red Flag 1: Lack of Leadership���������������������������������������������������������������������������18
Red Flag 2: The Wrong Leaders��������������������������������������������������������������������������21
Red Flag 3: Accidental Leaders���������������������������������������������������������������������������22
Not Everyone Wants to, or Should, Be a Leader��������������������������������������������������23
The Psychological Safety of Leaders������������������������������������������������������������������24
If Difficult Conversations Don’t Affect You, You Shouldn’t Be Having Them��������26
Sometimes to Show You Care, You Need to Show Your Teeth�����������������������������28
Summary������������������������������������������������������������������������������������������������������������29

iii
Table of Contents

Chapter 3: Culture�������������������������������������������������������������������������������31
Culture Is Not Free Beer, Fruit, and a PlayStation�����������������������������������������������31
Culture Contribution or Culture Fit����������������������������������������������������������������������32
What Does Autonomy Look Like for You?������������������������������������������������������������35
Process: The Enemy or the Hero?�����������������������������������������������������������������������37
Cut Only When Is Absolutely Necessary to Survive���������������������������������������������39
Find a Common Language����������������������������������������������������������������������������������43
Getting Past the Values Fluff�������������������������������������������������������������������������������45
Summary������������������������������������������������������������������������������������������������������������47

Chapter 4: Inclusion���������������������������������������������������������������������������49
Inclusion > Diversity�������������������������������������������������������������������������������������������50
Pitch at 80%��������������������������������������������������������������������������������������������������������53
Be Judged by Your Actions, Not Your Intentions��������������������������������������������������54
Get Under the Skin of Your Gender Pay Gap��������������������������������������������������������55
The Myth of Removing Bias��������������������������������������������������������������������������������60
Summary������������������������������������������������������������������������������������������������������������61

Chapter 5: Recruitment����������������������������������������������������������������������63
Respond to Every Single Job Applicant As Though Your Brand Depends on It����64
Start with Your Best Offer and Don’t Budge��������������������������������������������������������66
Your Candidate Experience Is As Important As Your Customer Experience���������69
Turn the Tables����������������������������������������������������������������������������������������������������71
Don’t Join This Company If…�����������������������������������������������������������������������������71
The Candidate Was Great! I’d Like to Meet a Few More Though�������������������������72
Summary������������������������������������������������������������������������������������������������������������74

iv
 Table of Contents

Chapter 6: Reward������������������������������������������������������������������������������77
Design for the 99%���������������������������������������������������������������������������������������������77
Pay Transparency������������������������������������������������������������������������������������������������82
The “Pay Me More or I’ll Leave” Ultimatum��������������������������������������������������������88
The Law Is the Floor��������������������������������������������������������������������������������������������91
All Benefits Are for Day 1������������������������������������������������������������������������������������92
You Probably Won’t Retire Early Because of Equity��������������������������������������������93
Minimum Leave, Not Unlimited Leave�����������������������������������������������������������������99
Summary����������������������������������������������������������������������������������������������������������100

Chapter 7: Learning��������������������������������������������������������������������������103
Water Your Plants����������������������������������������������������������������������������������������������103
Learning Is About Experiences, Not Just Knowledge����������������������������������������107
The “Best” Career Advice I Ever Received��������������������������������������������������������109
Approach with Planning: Peer Feedback����������������������������������������������������������113
The Perfect Resignation: When the Time Is Simply Right���������������������������������115
Summary����������������������������������������������������������������������������������������������������������116

Chapter 8: Performance��������������������������������������������������������������������117
The Trinity: What, How, Where?�������������������������������������������������������������������������117
I Messed Up OKRs, Twice!���������������������������������������������������������������������������������120
People Outgrow Startups; Startups Outgrow People����������������������������������������122
If I Hear “Hire Slow, Fire Fast” One More Time…���������������������������������������������125
The Death of Performance Reviews?����������������������������������������������������������������127
Summary����������������������������������������������������������������������������������������������������������132

v
Table of Contents

Chapter 9: Remote Working��������������������������������������������������������������135

The Covid-19 Acceleration��������������������������������������������������������������������������������135
Remote Work Is Uncovering Our Dirty Laundry�������������������������������������������������136
Know the Difference Between Flexible and Remote Work��������������������������������139
The Remote Manager����������������������������������������������������������������������������������������141
Burnout Is Our New Thanos������������������������������������������������������������������������������143
Summary����������������������������������������������������������������������������������������������������������144

Chapter 10: Your Career�������������������������������������������������������������������147

Know the Difference Between Who You Are and What You Do��������������������������147
Be Clear on What Your Role Is and What It Isn’t������������������������������������������������149
“I Don’t Know”��������������������������������������������������������������������������������������������������150
Find Your Outlet�������������������������������������������������������������������������������������������������151
Be Ruthless with Your Time������������������������������������������������������������������������������153
Everyone Is a People Expert������������������������������������������������������������������������������156
It’s Great to Experience a Truly Shit Company at Least Once����������������������������158
Scaling Part 1: Keep Your Team As Small As Possible���������������������������������������159
Scaling Part 2: Make Yourself Redundant���������������������������������������������������������163
Summary����������������������������������������������������������������������������������������������������������164

Chapter 11: TL;DR�����������������������������������������������������������������������������167

Too Long; Didn’t Read: A Summary of Text That Was Too Lengthy��������������������167

Index�������������������������������������������������������������������������������������������������179

vi
About the Author
Patrick Caldwell is a multi-startup People
& Operational leader with experience in
leadership teams and boards across Australia,
the United States, and Europe. Pat is currently
building out the first people and culture
strategy as the Chief People Officer at Send,
an InsurTech software company in the UK,
and also serves as a Non-Executive Director
on the board of ImpactEd, an EdTech scale-up
helping purpose-driven schools, educational
institutions, and partners with high-quality evidence and evaluation to
improve outcomes for young people. Hailing from the coal mining industry
in Australia, Patrick was formerly the COO at FundApps, an award-winning
B Corporation, and the VP People & Operations at Metomic, an innovative
cybersecurity technology startup.

vii
Preface
“Patrick should consider if HR is right for him. He seems frustrated most
of the time.”
My first reaction was “pfft, whatever” to this gem from a 360
assessment. I wouldn’t have been so frustrated if I felt like we were actually
having a positive impact on people. But I wasn’t. I was churning through
spreadsheets, lists of policies, and the odd disciplinary that made up my
days in what was jokingly (not really) known by a supervisor as the Human
Remains department. Honorable mention to his second favorite name, the
Hardly Relevant department.
This isn’t an exception. This is still what the vast majority of people
experience and come to expect from their HR department. The people
you speak to when something is wrong, or better put, the people you hope
to not need to speak to. Despite years of incremental change, we haven’t
yet shaken the compliance-driven, “on the employer’s side,” back-office
shadow that we’ve cast into businesses. And maybe we never will, at least
completely.
But this isn’t a book to bash HR, as therapeutic as part of me might find
that. It’s a book about what HR is becoming and the transformation of how
we think about people and culture. We’re part of a generation of teams,
leaders, and businesses demanding an entirely new breed of capability
around people and culture. We’re becoming People teams, relentlessly
focused on how we engage, develop, empower, and recognize people
and how our obsession with culture and the people experience can drive
businesses to success.

ix
Preface

I fundamentally believe in the coming years we’ll see People functions

entirely replacing what we’ve come to associate with traditional HR. Some
of that work will still need to be done, but it won’t be the purpose of the
People team, or how we add the most value to a business. We’ll no longer
be just partners and advisors to a business either. We’ll be in the business
and working on the business. We’ll treat our recruitment and onboarding
experience with the same focus, care, and attention that we do our sales
pipeline. We’ll be fully in sync with our people and looking for ways to
increase their success and nurture relationships in the same way our
customer success teams do. We’ll be working cross-functionally to design
and iterate our work in the same way we expect our Product teams to. And
we’ll be armed with the same tools and data insights that we’ve come to
expect from our technology teams.
My first experience with what is now demanded from People teams
came in startups. It’s not exclusive to startups, and they can receive a
disproportionate level of recognition around innovation in the people
space simply because they’re not the stereotype of a large business (shout
out to the People innovators in big businesses too!). Startups are, however,
a really insightful test for what will be in the years ahead.
In startups, every founding and leadership team experiencing growth
will at some point make a decision to introduce a People capability into
their team. There’s no baggage with this decision and usually no existing
team, processes, or ways of working that influence what a People team
can be in their business. Startups allow us to see how leaders answer this
question: When you can build it from scratch, what do you aspire for the
People team to be?
As I transitioned from the world of HR to the world of People, I also
met some truly incredible folks in both People roles and elsewhere in the
business, who have helped shape my perspectives and work for how we
engage, develop, empower, and recognize people. As passionate as I may
be about both people and culture, I’ll never be an expert and I don’t think

x
 Preface

that’s possible anyway. We’re constantly learning, adapting, and changing

how we think about people, and keeping up with that by itself, let alone
in high-growth startups, is a thrilling challenge. It also means I’ve had to
learn things the right way – by doing them. Sometimes they worked, and a
lot of the time they didn’t and I had to iterate my thinking and approach.
As quite a reflective person, I also found myself making mental notes
along the way. Things I observed, suggested, struggled with, worked on,
screwed up, or smashed out of the park all made their way into my mental
notes in the hope they might prove useful the next time I was faced with
a similar scenario. Over time, these mental notes became written notes,
throughout a myriad of notebooks, journals, and eventually a Notion page
of stuff I didn’t want to forget.
What you’ll find in this book are those mental notes I made along the
way. This is not a book bursting with management theory and frameworks,
rather a collection of stories, personal principles, and lessons learned.
It’s grounded in my experience and the experience of those I’ve been
fortunate enough to work with. I wrote these mental notes for me, but I’m
sharing with you in the same way I might if we were chatting at the pub.
And while every business is different, I hope there is something in here for
everyone at whatever stage you are.
If you are like me and have a short attention span, or don’t read books
cover to cover, I’d highly recommend starting with Chapter 11.

—Pat

P.S. It turns out HR was not right for me. But I think People Ops might
just be.

xi
CHAPTER 1

Building from Scratch

If you’ve joined a startup, or even interviewed at one, you’ll likely have
been sold the utopia of building on a blank canvas. That we have no
processes in place, no playbook to make our success repeatable, no idea
what we’re even doing. OK, maybe not that last one, but I’ll come on to
that later and why it wouldn’t be such a bad thing to tell people up front.
As incredible and liberating as a blank canvas sounds, it’s a myth.
Don’t get me wrong, I still get warm fuzzies anytime I think about building
things from scratch in a startup. But unless you are a founder starting a
company, there is no such thing as a blank canvas. The canvas is already
sprawled with paint around culture and leadership – existing beliefs,
norms, ways of working, expectations, personalities, conflicts, highs and
lows of everything that has happened before you showed up. The paint
might not look like a work of art, but it’s already there whether you like
it or not.
There are an endless number of ways that paint can be sprawled across
the canvas, but here’s a selection of some of my favorites from my early
days within various startups:

• The hiring engine that takes place through “who do we

know who could do this?” rather than “how will we find
someone who will be awesome at this?”

• Having no onboarding process because great people

onboard themselves.

© Patrick Caldwell 2023 1

P. Caldwell, People Ops, https://doi.org/10.1007/978-1-4842-9819-0_1
Chapter 1 Building from Scratch

• The employee who earns half of what they are worth

on the market but operates under the belief that in five
years the startup will be a unicorn and they can cash
out on their equity and retire early.

• Justifying the lack of job descriptions with the fact

people wear lots of hats in a startup.

• The founder who believes every employee who joins

should be as deeply invested and committed to the
cause as they are.

• The promotion of a mid-level individual contributor

to CxO after six months because they know the
product well.

• And, my favorite one, believing that they have a

learning culture because a few developers went to a
conference last year.
Sound familiar?
At the start of my time with every high-growth startup I’ve joined,
there’s a period for several weeks when I try to actively observe the paint
on the canvas. This is harder than it sounds, but the benefit of being so new
to a company is that you’re viewing that canvas from the perfect angle. You
haven’t been involved at all in painting it, so you have that beautiful mix
of objectivity and curiosity. In a short while, that objectivity is mostly gone
and you’re now also painting the canvas and getting stuff done.
For the next few months, the key to surviving a startup is to find
the balance on getting stuff done today and keeping one eye on what’s
coming next. You need to be tactical enough to stay off the “not right for
this stage of our growth” list, but thoughtful and strategic enough to be on

2
 Chapter 1 Building from Scratch

the “grow with us” list. And so here seems the logical place to start sharing
some of my musings with the hope you might make at least one less
mistake than I have.

Ground Your Decision-Making

I often wish managing people and building teams was more black and
white. Instead, we’re faced with various shades of gray and expected to
navigate through that with ease. Good judgment is important, but by itself
judgment can be too easily confused with an opinion. What makes this
easier is how you anchor your judgment in relevant data and information.
One of the frogs I try to eat very early in my time at any startup is
compensation. If the startup is bootstrapped, we have to operate within
very tight cash restrictions and that means making educated and informed
judgments on where we get the most bang for our buck when it comes to
compensation. If the startup is backed, the same principle should apply
too but with a wee bit more flexibility if the pockets you have are deeper.
Compensation is deeply emotional. If you’re in the tech industry, it’s
going to be the biggest area of your spend. If you’re in another industry,
it’ll be one of the top three areas of spend. So getting it right is critical.
But that’s just the company side of compensation. For us as individuals,
we don’t really care how much of the P&L is dedicated to compensation.
We just care about how much we get and whether it meets a few criteria
around right and wrong:

• Expectations: Does it seem right based on what

I’m expected to do? I’ve lost track of the number of
negotiations where the basis of the ask is their gut feel
on whether the package seems like it fits with the role.

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• Lifestyle: There are two points to this to be mindful of:

What was I earning previously and is this the same or
better? And what sort of lifestyle am I trying to live or
uphold? A software engineer from a big tech company
on $300k per year with a lifestyle around this is going to
find your offer of $200k to be unwelcome regardless of
how much data exists.

• Status and sense of worth: Never underestimate this. It’s

normal, human, and common to find a sense of worth
in our salary. For some people, it’s inconsequential. For
others, it’s everything!

• Fairness: I’ve framed most of the preceding criteria

in the context of a new starter considering their
compensation, but the fairness criterion is one of the
most vital considerations for the existing team. If you’ve
been in your role for a year, perhaps you had a small
bump recently, and you find out a new team member
doing the same role has joined and has a higher pay
than you, you’re likely going to be pretty down about
that regardless of their background.
I used to believe I could architect a perfect, data-backed model for
startup compensation. I’ve tried a few times, and each time I ended up
realizing something really important. Everyone supports a data-driven
approach to compensation, until the data conflicts with what they want to
be paid.
Over time, I started to accept that a bit of art in compensation was
never a bad thing – 80% science, 20% art. Put principles around how
compensation is determined and use data and benchmarks to inform that.
Use compa ratios or compensation ranges to build fairness into routines.
And, most importantly, communicate transparently with the team and
external candidates how compensation is set and reviewed.

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Not everyone will be a fan of this. Frankly, it’s usually the people who
benefited from what the system used to be. But achieving 100% support
is not the point here. You’re optimizing for something that creates fair,
equitable, and consistent compensation outcomes and sometimes that
means some tough reality checks for people. The key here is that having
your decision-making grounded in something objective, with a small
amount of flexibility to cater for the realities of such an emotional and
complex topic.

Simple Is Sexy
There is a certain urgency that people challenges tend to instill in a startup.
Unfortunately, urgency has a knack for distorting decision-making toward
the short term and that often comes back to bite you in the ass.
Let’s consider recruitment. You need to grow fast! You feel the pressure
from hiring managers. You find an amazing candidate who at the offer
stage wants to negotiate some bespoke terms in their contract like a
guaranteed bonus or a higher notice period. Maybe a different health
insurance package or some nuance in their commission plan. Agreeing to
these sorts of changes is often made out to be insignificant. A small price to
pay to land a candidate and fill that role you’ve been trying to for ages.
Let’s now add double- or triple-digit growth on top of that. Your team
of 80 is now 240 and you have the complexity of individual terms and
conditions to be administered on a much larger scale. It means the teams
and infrastructure needed to administer that complexity grow with it. And
don’t forget that people talk. So Joe will find out eventually that he has a
less attractive commission structure than Sally, and Sally will learn that
Kate has a benefit that you asked for but were told you couldn’t have.
You get the point. Simple is sexy. And grossly underrated.

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When it comes to employment terms in a growing company, there is

a lot to be said for simple, consistently applied terms across the broadest
remit possible – that includes notice periods, leave entitlements, benefits,
commission plans, bonuses, and anything else you might expect to be
negotiated into an employment contract. There will always be some
variability due to regional differences if the team grows globally, so if you
have the luxury to join a company early before a period of hyper-growth,
consider what the default offering looks like across as many employment
terms as possible and don’t budge.

Done > Perfect

Outside of startups, there’s a fairly common way of working in the People
space. You table ideas and put together proposals with hope that senior
leaders will approve it. You write extensive business cases justifying
ROI and book meetings with key stakeholders looking for feedback and
ambassadorship. You’ll have a communication strategy in place which in
turn will generate communication and implementation plans. And finally,
you’ll have a feedback and review cycle on your initiative to remind senior
leaders of how well it’s performing.
I used to work in this way. For years. I know of a number of people who
have built their careers around their ability to thoroughly and methodically
plan for every circumstance and they rarely spend time actually executing.
Then I ended up in startups where most of that work is more
insignificant than I cared to recognize. I’m not suggesting engaging
stakeholders and being thoughtful about strategy isn’t important, just that
the difference between a good initiative and a near-perfect initiative is of
very little consequence in a startup. It’s likely why we’ve ended up with so
many “get shit done” company values that prioritize execution and pace.

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In startups, having something in place that’s about 80% done is of

far more value to the company than waiting weeks or months until it’s
perfectly complete. The more potent realization for me was that anything
you build you’ll likely need to upgrade or replace a number of times
anyway as the company grows. After all, if you’re doubling headcount year
on year, what you build in year one for 100 people is likely going to need a
lot of iterating to still be effective for 400 people in year two.
There is undoubtedly a long line of “but what about this?”
considerations. The goal of prioritizing done over perfect is not about
neglecting some of the key steps to change, in particular around
communication, engagement, and influencing leaders. The goal is to get
the initiative to a point where it’s solving a problem or delivering value,
and then approaching it with a mindset to iterate and improve once it’s in
place. Here are a few things to clarify early to set this up for success:

1. Is the initiative aligned with what the company

is trying to achieve? There are 10,000 things we
probably could be doing. Find the two to three most
important ones that help the company achieve
its goals. This will speed up how you engage and
influence.
2. How will you communicate the initiative in a few
different ways? Skip the vanity social media posts
and five-slide cascading communication plan. The
key here is to answer the question: How will every
team know about this? In many startups, a combo
of async messaging tools, all-hands and stand-up
routines, intranet pages, and a bit of rinsing and
repeating will do the trick.

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Chapter 1 Building from Scratch

3. Do you have a rough idea what success looks like?

This needn’t be a set of objectives and a pyramid of
key results. What’s the most important thing you’re
solving for and how will you know you’ve done
that? Focus on that when you’re communicating to
leaders and the team.

4. How will you set expectations? In a number

of startups, I’ve used the symbol of a naming
convention to many of the bigger initiatives.
Parental Leave 3.0. Reward 4.0. Leadership
Development 2.0. It’s designed to represent
iterations and over time becomes a symbol for every
initiative being considered as an improvement area
in the months and years to come.

Self-Service FTW
There’s a small window in the early days of startups where you can get
away with highly unscalable solutions. In fact, there’s a lot to be said for
why you should embrace unscalable solutions for as long as possible
especially if there’s a highly personal and human component to it.
When you have 10 or 20 employees in your startup, you might not be
too concerned with managing leave in a spreadsheet, recruitment through
emails, and processing the odd expense claims when someone in the team
sends you a photo of their stand-up desk receipt. I’m not sure exactly where
the threshold is, but there’s a point in growing the team when the burden of
this administrative work becomes too much of a distraction on people in the
company who are likely managing people stuff in addition to their core roles.
The most common answer to this is “let’s hire someone to do the
work” which, despite the excitement that growing a team involves, is often
just managing a symptom of a growing team rather than the problem

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itself. The question is not “who manages this work” or “how do we cope
with increased administrative work” but rather “how do we reduce the
administrative overhead our growing company is producing.” Hiring is
still a possible solution, but it’s the last possible solution as the goal is
ultimately to keep the smallest team for as long as possible.
For a lot of the administrative work a growing startup encounters –
expenses, leave, payroll, access to systems, etc. – I’ve found a lot of
success in using tools to drive self-service. Allowing team members to
manage their own administrative workload in a clear and accessible way,
supplemented with tools that automate as much of the process as possible.
There are cheap, even free, HR tools on the market to administer leave and
benefits including payroll inputs.
Similarly, automation workflows can help support onboarding and
offboarding procedures and distribute actions automatically across the
team after a trigger is passed. Central knowledge management tools
provide a single source of documentation and process so that the team
can self-serve the “know-how” of the company which saves a lot of back
and forth communication and even the need to run training sessions
sometimes too. The outputs of this work will still exist but only a fraction
of the work that originally existed, so this can either still sit as part of
someone’s role or can be outsourced to an accountancy, payroll, or virtual
assistance company for a few hours per week.
There will still come a time where the People, Finance, and Operations
areas will need dedicated in-house capability, or at least fractional where
more strategic work is needed, but putting in place efficient tooling that
automates administrative work and encourages self-service will delay that
need which is important. It will also mean that when the time comes to
hire into these teams, there is space for a more strategic hire that can focus
on the highest value initiatives to the success of the business rather than
just consolidating the administrative burden into them.

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Decision by Committee Sucks

We had just concluded a recruitment process for a senior software
engineer. The process involved a number of team members who were
involved in the various assessment and interview stages. We came together
for a quick debrief after compiling our recommendations individually,
only to find a rough split across the team. Four people had suggested a
yes to hire, and two people had suggested no. We had two attempts at
this debrief to come to a decision with the manager clearly looking for a
group decision. In the end, the manager decided that as the group couldn’t
come to a single decision, that it was a “no” decision for that candidate.
This same process happened for a number of candidates. When the
recommendations were unanimous, we proceeded quickly. But when it
was not unanimous, we defaulted to no.
Now, there’s no saying whether each decision was right or wrong but
that’s not the point. The point is that a pattern existed of us delegating
decision-making authority to a large group of people and setting the
expectation for those people that they were operating as a committee.
It was probably more like a jury in practice, but let’s keep going with the
committee analogy.
That decision-making process within the committee was poorly
executed and the result was a slow and inefficient process and high risk of
a poor-quality decision too. There are several reasons for this:

• Recommendations were coming from people involved

throughout different stages of a recruitment process.
Those who were completing the technical assessment
were evaluating on a different set of criteria to those
completing the pair programming assessment, and
those doing the cultural interview. It meant the
recommendations were ultimately apples and oranges,
each grounded in different explicit and implicit criteria.

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• We did not distinguish between feedback and

recommendations. We sought recommendations from
the team when what we actually needed was input to
the recommendation. This set poor expectations for
the team too, who initially responded positively to the
opportunity to play a bigger role in hiring efforts, as
they were often investing huge amounts of time into a
recruitment process and seeing very few people emerge
successful from it.

• We made a poor assumption that candidates needed

to tick every box. If a candidate performed really well
in all but one part of the recruitment process, the team
member who was in that one part of the process is only
looking through a very narrow window into how that
candidate may perform in the role.

• There was a bit too much desire to please and

agree from me, and likely the manager too, so if
the committee was split, we defaulted to the more
conservative option and encouraged the team that next
time would be different.
This example is rooted in a recruitment process, but very similar
behaviors happen throughout all sorts of team routines too. Picture the
leadership team who struggle to agree a way forward because some people
aren’t on board. We idealize consensus and agreement which doesn’t lead
to high-quality decisions. Or fast ones.
We made a lot of changes to our recruitment process to focus on
how we were making decisions. Most of these changes apply to broader
forums too:

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• Clarity: Identify the decision-maker who is solely

responsible for making the call. They should be
the person who is accountable for the result of that
decision.

• Expectations: Set expectations with other team

members for what role they will play. In the
recruitment debriefs, we let team members know
the debrief will be to share their notes, observations,
examples, and any concerns relating to the part of the
process they were involved in.

• Partnership: Establish the People team as a partner to

that decision, helping the decision-maker consider the
feedback and input and prioritizing what is important.

• Get it done: Make the damn decision! As you will have

just read, done trumps perfect and all decisions carry
risk. So make yourself comfortable with that risk and
make a call. We won’t get them all correct, but it’s still
better than indecision.

• Communication: Communicate the why behind the

decision and genuinely recognize the input, whether it
supports the decision or not.

Beware the Magpies

If you’re unfamiliar with magpies, they are a beautiful black and white
bird with a reputation that precedes them. Magpies are known for their
attraction to shiny objects. Whether that’s actually true or not, and how
magpies actually perceive shiny objects, is beyond my knowledge. When
I was growing up in Australia, we would ride our bikes up and down

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the street wearing brightly colored and sparkled helmets which would
encourage magpies to swoop and attack us. Seems pretty stupid in
hindsight.
Many years ago in the early days of my HR career I had a colleague
who described me as a magpie. I suspect it was meant as a subtle insult
but it’s something that has stuck with me for a while, both in terms of the
underlying message but also reflective of my behavior at the time. I was
an absolute sucker for opening up a magazine or LinkedIn, reading about
something I thought was really cool, and coming to work the next day
and wanting to implement it. A sales team with no commission structure?
LET’S DO IT! An entire company without reporting lines and job titles?
LOVE IT! An entire company where you get to set your manager’s, and the
CEO’s, pay? WHERE DO I SIGN UP?!
It might come as no surprise that once I joined my first startup, my
magpie personality started to reemerge. Faced with an environment that
was all about moving at pace, iterating, experimenting, and innovating, my
ears would prick up at any talk of the next revolutionary working practice
or something I heard at a conference or read online. This time around,
however, I was a bit more aware of what was happening and needed to find
a way to harness the magpie spirit without forgetting there’s a context and
thoughtfulness needed to make something work in that specific startup.
I started to build mental lists of what was happening within the
industry and the major shifts facing employers – from the rise of flat
operating structures to increased benefit flexibility, to really innovative
learning and performance solutions. I was consciously avoiding copying
and pasting the new, shiny ideas I was seeing elsewhere and starting to
think about what I could learn from those ideas and in what context there
would be value to rethinking our current approach.
I remember in the early days of a startup we were discussing learning
cultures and how to really ignite the curiosity and passion for learning
within the team. We had budgeted for training but the budget was rarely

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used. There were also some conferences and workshops we paid for
but only for a very small number of the team who had put their hand up
and really pushed for it. This was also around the same time as we saw
the emergence of payments platforms that let you distribute budgets for
flexible benefits. Bingo! We put in place a learning budget that allowed
people to use virtual payment cards to self-service their own learning
resources. We removed the perceived barrier around needing to ask for
permission by removing all approvals and trusting that people will do the
right thing (98% of people did), and we integrated with a learning Slack
channel to automatically share what everybody was investing their budget
in. This was also a team accountability step – if you bought an iPhone with
your learning budget it would be posted on Slack for everyone to see.
What transpired after this was pretty special. People started making
recommendations to each other on useful learning resources. Small
teams started forming to participate in group workshops and conferences
together. We set up a company library of resources and playlists to help
folks interested in learning new skills. And it operated itself, with almost no
involvement from the People team.
Beware the magpies. There are a lot of us, and left unchecked, we are
directing energy into things that are not driving genuine value in a startup,
or any company for that matter. Help us build context for initiatives and
steer us back on course if the excitability is not grounded in what’s actually
important in the company.

 our People Strategy Is Your

Y
Business Strategy
I once worked in a team where we presented the People strategy to the
company before the business plan was finalized. Which in hindsight feels
a bit odd. Where did the people strategy come from exactly? How did we

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 Chapter 1 Building from Scratch

manage to identify where to focus our time, and communicate why that
was the case, when we didn’t yet have a broader business plan to guide the
direction of the company?
While it took a few detours through teams like that one, I’ve come to
learn that the people strategy is an enabler of the business strategy rather
than a stand-alone strategy itself. There isn’t a single pillar of a startup’s
strategy, or a single team within a startup, that doesn’t have a significant
component of their success directly related to people. Be it ramping up
customer success teams to deliver an exceptional, global experience for
customers. Or maturing a reward framework to drive a more predictable
cost curve. Or planning the growth forecast for investors to ensure there is
adequate, ramped sales capacity to deliver revenue goals.
I no longer invest huge portions of my time, even as a Chief People
Officer, designing a long-term people strategy. Instead, time is invested
in getting under the skin of all parts of the company, understanding
the challenges and performance drivers, and considering how people
solutions will drive the success in that area. And then we make it happen.
This reversal of approach does not dilute the people-first approach in
any sense, but rather offers significantly more buy-in around the work
that needs to happen when it directly impacts the performance of the
company.

Summary
• Ground your decision-making in data and make it
transparent. The goal is not to please people. Good
decisions sometimes piss people off.

• Avoid short-term temptations for bespoke employment

terms. You’ll build a people debt that comes back to
bite you in the ass once you grow.

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Chapter 1 Building from Scratch

• Perfect work rarely delivers materially more value than

good work in a startup, so get it done and trust your
ability to iterate it over time.

• Build automation and self-service into as many

administrative processes as possible to delay your need
to hire and reduce administrative burden.

• Be clear on how decisions are made and what inputs

are needed. Decision by committee is neither fast nor
does it result in a higher-quality decision.

• Every initiative you work on must be aligned to the

priorities of the company. Work your way inside out to
understand what people solutions will solve challenges
and enable success in each team. And beware magpies!

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CHAPTER 2

Leadership
In the last chapter, we covered the myth that is the blank canvas we’re
building from and the paint that already exists on that canvas. Arguably the
biggest source of paint and the state of the business you’ve joined will be in
the leaders that are already in place. So in this chapter, I want to get under
the skin of startup leadership which, unsurprisingly, appears frequently in
my mental notes.
I have several shelves of leadership books in my home. Most of them
have imparted nuggets of wisdom or know-how into my brain, yet despite
having read so many leadership books, I still can’t say with any confidence
they actually prepared me at all for the realities of leadership positions.
The recognition that leadership is not a position is well understood, but for
the purpose of this chapter when I use the word leaders, I am referring to
those who are leading a team.
An investment in leadership is hard work, but well worth the return. It
might take a combination of developing existing leaders, promoting from
within and hiring externally. In many small companies, even before people
leaders are in place, they are seen as a hierarchy and structure, regardless
of the person and their style. Being clear on the “why” helps as does
casting a vision forward to how the company will grow over time. Most
importantly, it’s a recognition that leaders cast a shadow that runs deep
into a company, especially a startup, so it’s vital that shadow is having the
best possible impact on the team.

© Patrick Caldwell 2023 17

P. Caldwell, People Ops, https://doi.org/10.1007/978-1-4842-9819-0_2
Chapter 2 Leadership

There are several parts to this chapter that cut across the People
remit. So for that reason, I’ve kept the focus on some of the key leadership
challenges that exist in a startup, kicking off with my three red flags. These
red flags are three things that are constantly sitting on my radar from the
moment I start with a company. When you get these right, the value is
immeasurable. When you screw it up, like I have a few times, the damage
takes a long time to recover from.

Red Flag 1: Lack of Leadership

Before you immediately think this is rubbish and startups do not
need more leaders, it’s certainly not lost on me that startups need a
disproportionate number of driven and capable individual contributors
compared to leaders. But let’s cast back to when a startup is 20 or so
people. In the initial, scrappy phases, the founder(s) were likely the
leader for everyone in the company. Even at 20 people it’s quite normal
for most people to be reporting to a founder, or at best there might have
been an early leadership hire into a sales, operations, or technical team.
As the team grows to 50 or enters the journey after Series A funding, the
roles and expectations of leaders fundamentally change. There is now a
need for leadership beyond the founder(s) who are also transitioning into
operational roles as C-level or senior team members.
During this phase, spans of control often balloon. It’s not uncommon
for one or many founders to have teams that are 10, 15, sometimes 20
people strong. Temporarily you can cope with a large span of control
before you usually see symptoms that it’s time to outgrow that founder-
central leadership structure. Your team will start to demand functional
expertise and mentorship. Founders will start to end up with remits that
are far too wide and result in ineffective leadership or burnout. Investors
will start to look for a transition away from founder-led success to

18
Another random document with
no related content on Scribd:
therefore, expand, and in order to regain a density a thousandfold
less the radius must expand tenfold. Energy will be required in order
to force out the material against gravity. Where is this energy to
come from? An ordinary star has not enough heat energy inside it to
be able to expand against gravitation to this extent; and the white
dwarf can scarcely be supposed to have had sufficient foresight to
make special provision for this remote demand. Thus the star may
be in an awkward predicament—it will be losing heat continually but
will not have enough energy to cool down.
One suggestion for avoiding this dilemma is like the device of a
novelist who brings his characters into such a mess that the only
solution is to kill them off. We might assume that subatomic energy
will never cease to be liberated until it has removed the whole mass
—or at least conducted the star out of the white dwarf condition. But
this scarcely meets the difficulty; the theory ought in some way to
guard automatically against an impossible predicament, and not to
rely on disconnected properties of matter to protect the actual stars
from trouble.
The whole difficulty seems, however, to have been removed in a
recent investigation by R. H. Fowler. He concludes unexpectedly that
the dense matter of the Companion of Sirius has an ample store of
energy to provide for the expansion. The interesting point is that his
solution invokes some of the most recent developments of the
quantum theory—the ‘new statistics’ of Einstein and Bose and the
wave-theory of Schrödinger. It is a curious coincidence that about
the time that this matter of transcendently high density was engaging
the attention of astronomers, the physicists were developing a new
theory of matter which specially concerns high density. According to
this theory matter has certain wave properties which barely come
into play at terrestrial densities; but they are of serious importance at
densities such as that of the Companion of Sirius. It was in
considering these properties that Fowler came upon the store of
energy that solves our difficulty; the classical theory of matter gives
no indication of it. The white dwarf appears to be a happy hunting
ground for the most revolutionary developments of theoretical
physics.
 To gain some idea of the new theory of dense matter we can
begin by referring to the photograph of the Balmer Series in Fig. 9.
This shows the light radiated by a large number of hydrogen atoms
in all possible states up to No. 30 in the proportions in which they
occur naturally in the sun’s chromosphere. The old-style
electromagnetic theory predicted that electrons moving in curved
paths would radiate continuous light; and the old-style statistical
theory predicted the relative abundance of orbits of different sizes,
so that the distribution of light along this continuous spectrum could
be calculated. These predictions are wrong and do not give the
distribution of light shown in the photograph; but they become less
glaringly wrong as we draw near to the head of the series. The later
lines of the series crowd together and presently become so close as
to be practically indistinguishable from continuous light. Thus the
classical prediction of continuous spectrum is becoming
approximately true; simultaneously the classical prediction of its
intensity approaches the truth. There is a famous Correspondence
Principle enunciated by Bohr which asserts that for states of very
high number the new quantum laws merge into the old classical
laws. If we never have to consider states of low number it is
indifferent whether we calculate the radiation or statistics according
to the old laws or the new.
In high-numbered states the electron is for most of the time far
distant from the nucleus. Continuous proximity to the nucleus
indicates a low-numbered state. Must we not expect, then, that in
extremely dense matter the continuous proximity of the particles will
give rise to phenomena characteristic of low-numbered states?
There is no real discontinuity between the organization of the atom
and the organization of the star; the ties which bind the particles in
the atom, bind also more extended groups of particles and
eventually the whole star. So long as these ties are of high quantum
number, the alternative conception is sufficiently nearly valid which
represents the interactions by forces after the classical fashion and
takes no cognizance of ‘states’. For very high density there is no
alternative conception, and we must think not in terms of force,
velocity, and distribution of independent particles, but in terms of
states.
 The effect of this breakdown of the classical conception can best
be seen by passing at once to the final limit when the star becomes
a single system or molecule in state No. 1. Like an excited atom
collapsing with discontinuous jumps such as those which give the
Balmer Series, the star with a few last gasps of radiation will reach
the limiting state which has no state beyond. This does not mean
that further contraction is barred by the ultimate particles jamming in
contact, any more than collapse of the hydrogen atom is barred by
the electron jamming against the proton; progress is stopped
because the star has got back to the first of an integral series of
possible conditions of a material system. A hydrogen atom in state
No. 1 cannot radiate; nevertheless its electron is moving with high
kinetic energy. Similarly a star when it has reached state No. 1 no
longer radiates; nevertheless its particles are moving with extremely
great energy. What is its temperature? If you measure temperature
by radiating power its temperature is absolute zero, since the
radiation is nil; if you measure temperature by the average speed of
molecules its temperature is the highest attainable by matter. The
final fate of the white dwarf is to become at the same time the hottest
and the coldest matter in the universe. Our difficulty is doubly solved.
Because the star is intensely hot it has enough energy to cool down
if it wants to; because it is so intensely cold it has stopped radiating
and no longer wants to grow any colder.
We have described what is believed to be the final state of the
white dwarf and perhaps therefore of every star. The Companion of
Sirius has not yet reached this state, but it is so far on the way that
the classical treatment is already inadmissible. If any stars have
reached state No. 1 they are invisible; like atoms in the normal
(lowest) state they give no light. The binding of the atom which
defies the classical conception of forces has extended to cover the
star. I little imagined when this survey of Stars and Atoms was begun
that it would end with a glimpse of a Star-Atom.
Printed in England at the OXFORD UNIVERSITY PRESS
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