How to hire the right Head of People (and why others fail)

For most founder CEOs, hiring a first Head of People feels like a meaningful milestone – a signal that the company has reached a level of scale and complexity where founder-led people management is no longer sustainable. The team is bigger, the organisation needs more clarity over roles, more consistency in performance, stronger managers, more scalable hiring processes, better onboarding, and more deliberate thinking around culture and performance. At that stage, it is generally well understood that a strong Head of People should help address those things, and a talented one often can.

A strong Head of People can help a company attract better talent, support leaders to become more effective, bring more structure to performance and progression, strengthen the employer value proposition, and help lay the foundations for healthier, more sustainable scale. The difficulty is that hiring one successfully is far less straightforward than it might appear, and in our experience working with startups and scaling businesses, these hires fail with a frequency that founders rarely anticipate.

When they do fail, the reasons are usually quite predictable. It is rarely because founders naively assumed one hire would solve everything overnight. More often, it is because they hired the wrong person for that stage and/or were not fully prepared for the level of trust, alignment and empowerment the role requires in order to work. That matters because the first Head of People hire is unlike many other leadership hires – you are not simply bringing in functional expertise, but someone who will touch all functions; shaping how the company attracts, retains and gets the best from its people – affecting all teams.

These are issues over which the leaders and, in particular, the founding team, often hold strong existing opinions and beliefs. The incoming Head of People will need to influence the founder and leadership team on issues that are often central to how they think about the business, including hiring quality, culture, leadership behaviour, working style, performance, and the way the company evolves as an employer.

Hiring for early-stage suitability

When founder CEOs begin the search for their first Head of People, it is understandable that they are drawn to reassuring signals – a well-known brand on the CV, a senior title, experience in a high-growth company, someone polished and credible during interview, who seems to bring genuine gravitas to the room. Those things can all be useful, but they are not sufficient on their own, and they are frequently mistaken for evidence of suitability, which is where the problem begins.

The real question is whether they are right for the specific stage the company is at and the nature of the challenge it needs them to solve. A first Head of People in a startup or scale-up is usually walking into genuine ambiguity – no mature infrastructure, potentially no established team beneath them, reactive processes, limited people data, inconsistent management quality, and a founder who quite understandably still holds strong views on most people-related matters. They will need to decide quickly where to focus first, what can wait, how to build trust, and how to create meaningful impact without introducing unnecessary distraction or complexity.

That is a fundamentally different challenge from joining an established business with specialist teams, clearer systems and stronger internal support. Candidates moving directly from large corporate environments can sometimes struggle to make that transition – not because they lack capability, but because they are accustomed to operating with more infrastructure, more resources and more defined boundaries than an early-stage business can offer. Pedigree is a useful signal, but it should never be mistaken for a guarantee of fit for this stage, unless coupled with other key characteristics that prove necessary to succeed at this early-stage of a company’s growth.

The need to be hands-on

One of the clearest indicators of whether somebody is likely to succeed in a first Head of People role is whether they are truly comfortable operating at a detailed, practical level – and while that might sound obvious, it is one of the sharpest dividing lines in practice. A good startup Head of People cannot treat operational work as beneath them or arrive expecting a large team, polished systems and plenty of support. They need to be willing to get into the detail, understand where things are breaking, and work through the practical realities of improving them.

At the same time, they cannot be purely operational. They also need to be capable of frequently stepping back, interpreting the business strategy, anticipating the organisational implications of growth, and making clear-eyed decisions about where the People function can have the greatest commercial impact. Too much strategy and not enough execution, and they fail to build credibility. Too much execution and not enough strategic judgement, and they risk becoming a capable administrator rather than a high-value leader.

Commercial acumen is crucial

This is consistently one of the biggest differences between an adequate Head of People and a genuinely effective one. A startup Head of People needs to understand the commercial engine of the business they are joining – how it makes money, what the growth strategy is, where the pressure points are, what talent it needs in order to succeed, and what trade-offs the leadership team is managing. Without that understanding, it becomes very difficult to build real influence or earn the trust of a founder who is rightly focused on commercial outcomes.

In most startups, the People function does not automatically command authority – it has to earn it. The founder and leadership team need to feel that the incoming Head of People understands the mission, understands the constraints, and is capable of making judgements that help the business scale more effectively rather than introducing work that feels detached from growth. 

This is especially important because founders are often rightly cautious about anything that feels bureaucratic or performative. They are not opposed to investing in people, but they want to understand the commercial logic of what is being proposed, why it matters now, and how it should improve outcomes. A strong Head of People understands that instinct and works with it – not just bringing ideas, but explaining why a particular change matters, what problem it is solving, how success should be measured, and why the business should prioritise it at this moment.

A builder

A Head of People who is to be effective in a start-up must possess the ability to build without much existing infrastructure in place – something that is disproportionately harder than tinkering with and improving existing systems. They do not necessarily have to have operated at this exact stage before, but they need to demonstrate that they can operate pragmatically without waiting for ideal conditions. 

In many ways, the best startup Heads of People have something of a hacker mindset. They are resourceful, curious and self-sufficient – consistently seeking out the best available tools, drawing on their network for advice and perspective, and finding pragmatic solutions that fit the current stage of the business without over-engineering processes that will need to flex as the company grows. They are not reaching for expensive consultants or enterprise-grade systems before the organisation is ready for them. They are making intelligent, considered decisions about what is good enough for now and what can be built upon later – and that combination of pragmatism and forward-thinking is what separates a People leader who builds well from one who either under-delivers or creates unnecessary complexity too early.

In some cases, the founder hires someone they believe should be able to move the company forward, but that confidence begins to erode once the person is in the role. The Head of People fails to demonstrate sufficient commercial understanding, does not interpret the company strategy convincingly enough, or brings recommendations that feel under-evidenced, poorly timed or disconnected from the actual priorities of the business. In other cases, the dynamic runs in the opposite direction — the Head of People is capable, but the founder is not truly willing to create the space required for them to do the job well, continuing to micromanage, override decisions, or dismiss recommendations before they have been properly considered.

When the hire starts the break down

When the aforementioned criteria isn’t matched properly, we begin to observe a breakdown of the relationship between the CEO and the Head of People, which manifests a lack of values alignment. 

A new Head of People typically arrives with a view on how things should be done: how people should be recruited, how performance should be managed, how much flexibility should exist in the way people work. Some of those views will inevitably sit in tension with the founder’s own instincts and preferences, and that tension, if not handled well, tends to compound over time. 

The Head of People begins to feel undermined, sensing that their recommendations are being consistently dismissed or diluted, potentially, without proper consideration. The founder, meanwhile, grows frustrated that the person they hired does not seem to fully grasp what the business needs. 

It is worth being clear that this dynamic is not always the founder’s fault. Sometimes the Head of People is simply not commercially aware enough, or not a strong enough communicator, to build the credibility required to bring the leadership team with them. Making a compelling case for change requires data, context and an ability to connect People initiatives to business outcomes – and not every Head of People has that skill in sufficient measure. 

Nonetheless, regardless of where the fault lies, the outcome tends to be the same: a gradual erosion of trust between the CEO and the Head of People that, left unresolved, almost always ends with the Head of People leaving, one way or another.

Our view is that for a CEO recruiting a Head of People, they should approach the hire as they would if they were hiring for an executive coach, with whom they tend to work together for a long time. A relationship that requires genuine trust, candour, enough chemistry for both sides to be open about what matters to them and what frustrates them, and enough mutual respect for disagreement to remain productive rather than becoming defensive. If that foundation is missing, the hire becomes fragile very quickly.

The best interview process tests judgement and values-alignment

One of the more reliable ways to make a poor hire in this space is to over-index on how a candidate sounds rather than how they actually think. A polished candidate can speak very convincingly about culture, engagement, leadership development and employee experience without necessarily having the practical judgement required to build the right People function in a specific business at a specific stage. Getting beneath that surface requires an interview process built around specific examples – what the candidate personally identified and drove, what constraints they were working within, how they influenced the relevant stakeholders, and how they knew whether what they had done had actually worked.

Practical exercises are often more revealing still. Giving a candidate real or fictional company data and asking them to diagnose the situation, prioritise their response and explain how they would measure progress will typically tell you far more than any well-prepared answer. 

References, handled well, can be equally valuable – particularly for understanding whether someone has genuinely built from scratch before, influenced demanding stakeholders, and operated effectively in an ambiguous, fast-moving environment.

The founder has to be ready too

Perhaps the most important and most frequently underestimated variable in all of this is whether the founder is genuinely ready for the hire to succeed. Hiring a strong Head of People is not just about whether the candidate is capable enough – it is also about whether the organisation, and the founder in particular, is prepared to create the conditions that will allow the role to work.

People-related matters sit very close to the heart of most founder CEOs. How hiring is done, how performance is driven, how culture evolves, how standards are maintained — these things feel tied to the identity and future of the company in a way that makes them deeply personal as well as strategic. 

A founder can genuinely believe they are ready to empower a Head of People and still find, once the person is in the seat, that handing over that territory is harder than anticipated. That does not mean founders need to relinquish control entirely – nor should they, since a founder should always play a significant role in shaping the culture and standards of the business – but they do need to create enough room for the Head of People to experiment, challenge existing thinking, make changes, and genuinely influence how the company evolves, provided those proposals are thoughtful, evidence-based and grounded in the company’s strategy. 

Where founders consistently shut down recommendations that do not sit comfortably with their instincts, the role becomes very difficult to make valuable regardless of the quality of the person in it. The broader executive team matters here too – a Head of People who is tolerated rather than genuinely supported by the leadership group will struggle to build the credibility and influence the role requires to have true, meaningful impact.

What success tends to look like

When the conditions are right and the hire is made well, the impact can be significant. The founder regains time and headspace, managers become better supported to lead growing teams, hiring becomes more structured and consistent, onboarding improves, employees gain greater clarity about what is expected of them, and the People function shifts from being a reactive support service to a genuine source of commercial leverage – actively helping the business attract, retain and get the best from the talent it needs to grow.

The businesses that tend to see the greatest return from this hire share a few things in common. They go in with clear eyes, recognising that the role is not a fix-all solution. They hire for genuine values-alignment and stage-fit rather than solely impressive credentials (e.g brands on their CV), they give the person clear direction and appropriate guardrails, and then they truly empower them to do the job. Crucially, they foster a culture of candour between the CEO and Head of People – one where both sides can challenge each other, work through disagreement openly, and remain productive even when they do not see things the same way.

So how should a founder approach this decision?

The starting point is not the search itself, but an honest assessment of whether the conditions for success are genuinely in place. Is the organisation at a stage where this role can create real value? Is the founder ready to empower someone to lead the People function, or will they remain the real decision-maker on people matters in all but name? Is there enough clarity of direction, enough alignment within the leadership team, and enough genuine commitment to making the hire work?

If the answer to those questions is yes, then the hire is worth making – and worth making well. That means running a hiring process rigorous enough to reveal how a candidate actually thinks rather than how well they present and where else they have worked previously.

Done well, it is one of the most valuable hires a growing company can make, due to the incredible challenge of people matters at a growing company, and what a unique competitive advantage top talent can be. Done poorly, or before the right conditions exist, it can be a costly, time-consuming exercise and, with repeated failure, can leave a damaging impact on the internal reputation of the People function – ironically increasing the difficulty level of future Head of People hires further.

If you are interested in partnering with Hawkwood, an expert specialist in Head of People hiring on behalf of Tech scale-ups, you can enquire now via our contact form.