Treat people like volunteers: strategy implementation steps from Cathy Hawley of Bolster

The strategy implementation steps Cathy Hawley gives a leader joining a new company are unglamorous and precise: watch for 30 to 60 days, find out what people are actually experiencing, pick three priorities with your CEO, and tell everyone what you are deliberately not doing.

Hawley is a co-founder of Bolster, the executive talent marketplace, and spent 11 years at Return Path as chief people officer. She co-authored Startup CXO, which Fred Wilson described not as a book but as a field manual for building a management team and scaling a company. She is the first chief people officer to appear on this show.

Truck stops, domestic violence counseling, and DoubleClick

Hawley took an HR degree, largely because by the time she chose a major it was the only thing she could finish on schedule. Her first job out of college was HR manager at a truck stop, covering workers' compensation, payroll, benefits and every legal and equal opportunity issue that arose.

She thinks that would have been her career if she had not left the country. In the UK for several years, unable to find work in her field, she worked as a counselor for victims of domestic violence. She credits that period with changing the kind of HR leader she became.

Back in the US she moved through several HR roles before landing at DoubleClick, later acquired by Google, which she describes as her first real HR job at a technology company and the point at which she could start being a people leader rather than an HR leader.

Why the function changed its name three times

Hawley recognizes the police officer stereotype instantly. Someone notices HR is in the room and the conversation changes. Her response is that you should be having the same conversation whether she is there or not.

The naming history tracks the shift. Personnel became human resources so people would see the human in it, and then became people for the same reason. Language changed because practice needed to change.

Her explanation for why is about the workforce. In manufacturing environments, the job was largely writing rules and making sure people knew what to expect. With knowledge workers, that stopped being enough. You cannot retain people by offering a job, a paycheck and a benefits package. You have to understand their goals and motivations and build an environment around them.

She names the accelerants without pretending they were all noble. Large technology companies set new expectations for what a workplace provides. Social media made employer reputation public, so it is no longer your circle of friends who know what it is like to work somewhere, it is their circles too.

And she is honest about the real driver. What forces companies to change is whether they can attract and keep talent, and what that does to the bottom line. She does not love that framing, and thinks it is what actually happens: companies realize their competitive advantage is people, which obliges them to build practices, processes and values around them.

The CEO decides whether any of this is possible

Asked how Return Path built its reputation, Hawley starts with the founder and does not move on quickly.

Matt Blumberg started the company partly because of how badly he had been treated elsewhere, on the conviction that you can build a successful company and treat people well.

Her assessment of how much this matters is unqualified. She cannot overstate the CEO's importance here, and says that with CEOs who lack that value, it is genuinely hard to convince them to do right by people.

The evidence is in the hiring. Blumberg brought in a senior chief people officer, Angela Baldonero, at around 150 people, when most companies that size had one or two HR staff and nobody senior. Baldonero then hired Hawley as a director of people, which was also unusual at that scale, and Hawley had regular direct conversations with the CEO despite not reporting to him.

Her summary of what that bought her: she never had to make the business case. The investment was going to happen. Her job was to turn it into the right practices and programs.

Michael offers a data point on how far this has moved. A repeat founder recently hired a head of people operations as their fifth employee, on the reasoning that otherwise the culture becomes whatever it becomes. Hawley says that would have been unheard of five years earlier, and that at Bolster she now regularly sees startups prioritizing a fractional chief people officer alongside product and technical leadership, particularly when they are fully remote.

What separated the companies that got remote right

Hawley's account of the split is about mindset rather than tooling.

Many companies struggled at first because they never acknowledged remote might last. It was treated as a temporary necessity, with attention going to how quickly everyone could return.

The companies that did well asked a different question almost immediately: how do we embrace what we have and set people up to succeed in it. And then kept asking what is working, what is not, and what to adjust, running the equivalent of retrospectives on their own operating model.

She sees that even at CEO level now, with leaders describing a current approach as provisional and expecting to change it based on feedback.

Bolster's own example is instructive. They held a company offsite in November, when many companies were not gathering, with options and protocols. The value was not the event, it was what surfaced: they did not have enough social time. Their response was regional meetups and coworking days, calibrated by what people actually wanted, which turned out to be roughly monthly rather than constant.

Her framing of the underlying problem is one every distributed team faces. With twenty people you may have twenty slightly different preferences, so the work is finding what meets most people's needs.

On flexibility generally she has a stated bias and a stated limit. Not every role or company can be fully remote, and not everyone wants it. But she thinks some form of flexibility is now required to stay competitive, because work and personal life blend to a degree they did not before, and companies without it will find hiring and retention harder.

The partnership the COO should be building

Hawley's advice to CEOs who want to do right by people but do not know the next move is to build a genuine partnership with their people leader rather than a reporting line.

She notes, with amusement, that in their book Matt argues every C-level role thinks it is the one that partners closest with the CEO. Her own experience at Return Path was being the person he could bring something confidential to first.

The pairing she thinks is underrated is COO and chief people officer. Her stereotype, offered as a stereotype, is that people officers lean toward the people side and operating officers toward process, while acknowledging plenty of both cross over. The argument is that together they cover the whole operating system, and that building it around people and process at the same time is where the strength is.

Building an operating system for people you have not worked with

Bolster came out of a group leaving Return Path after the sale, wanting to work together again on something they cared about. The talent marketplace idea itself came from a couple of their investors, who assembled it and brought the team in.

With eight co-founders and many colleagues who had worked together for years, the interesting problem was the opposite of the usual one. How do you build an operating system for the people who were not there.

Their approach was to run it as a live experiment. The first two hires from outside Return Path were shown the existing operating system and asked what was missing, and their questions became the onboarding. That produced a deliberately lightweight process covering philosophy, values and how work happens.

The specific commitment they made is worth copying. Relationships come first, so a new person meets most of the company in their first two weeks. Hawley is explicit that this is not wasted time, because the relationship is a precondition for the work.

She is candid about the mistake underneath. With the original group they had assumed everything, because after years together that is just how you do things. The first outside hires absorbed the cost of those assumptions, and were strong enough people, and clear enough that they wanted a self-managed environment, to be good testers.

On values, the process was faster than Michael expected and Hawley confirms it. What did not work before, what we want to keep, what else needs saying. Done in the first week and then iterated.

They also wrote operating principles specifically to counteract their own known weaknesses. The team's shared tendency is to make things more complicated than they need to be, so one principle is simply to be simple.

At the November offsite they revisited everything with the whole company present. The values survived, the wording changed, and they finally named their philosophy. They knew they were non-hierarchical and preferred self-management but had never defined it, so they invented a term: a mostly self-managed organization.

Treat people like volunteers

This is the idea from the episode I expect to stick.

Hawley's long-held philosophy is that you should treat people as though they are volunteers, because they have a choice about whether to stay. The alternative posture, that you work for me and I pay you so you will do this, is the one she rejects.

Asked what that means in practice, her answer is about co-creation rather than instruction. Less telling people what to do daily, more bringing them along and building the environment together. She is realistic about scale, noting that a 500 person company cannot put everyone in a room to set goals, but that people should be co-creating at least part of what they do each day.

The effect she is aiming for: showing up because you want to, having helped shape what you are doing, rather than because you were told to.

Her volunteer test is the useful part. If an organization wants you back, it makes sure you are having an impact and finding some joy in the work, because it has bothered to learn what matters to you.

Measuring the culture you actually have

Hawley's method for evaluating culture is to go and ask, through surveys and through conversations, because what you want the culture to be and what it is may be two different things.

The questions are simple. What are people experiencing when they come to work. How are they treating each other. What do they love and what do they dislike.

Return Path ran an annual survey, and her example shows what to do with the results. One year the finding was that career development was dragging engagement, because tools existed but nobody knew about them. That became a top team goal for the quarter, with the explicit expectation that the score would move by the next one.

Her instruction to leaders watching attrition is blunt. Do not point at the people leaving. Ask what you need to do differently so people want to stay, and what environment you are creating.

She is particularly sharp on the retention counteroffer, having heard the example the week before. Someone says a 5% raise would have kept them. Her question is why it ever reached the point where 5% was enough to move them. Was it really the money, or not loving the work, or not feeling seen and heard, or not getting the leadership they needed.

Designing levels without over-engineering them

Hawley would prefer not to need titles, and observes a general drift toward generic rather than level-based ones. But at Return Path they eventually introduced levels because the company was large enough and enough people were asking, and she is pragmatic about why: people need it for their own record of what they have done.

Her design has two axes. Functional expertise, meaning the skills to do the job. And leadership, meaning both capability and behavior: whether you lead yourself and others, whether you communicate well. In short, what you get done and how you get it done.

Both matter, because promoting someone technically excellent but difficult to work with, inside a collaborative company, produces a mismatch.

The practical requirement is articulating the difference between levels. At Return Path they defined four levels of leadership behavior, from what is expected at entry level through to a senior executive, with the steps in between. On the technical side, the point is that you should know what the next level requires even if you are not being promoted to it, because that gives you something to aim at.

Her two warnings come from experience. Transparency, and do not over-engineer it. Their first version was elaborate enough that reviews took hours, which she attributes partly to having engineers help design it. The next iteration was simple enough that a peer could look at someone and say yes, I see them doing those things.

Her standard is not universal agreement but defensibility. If someone asks why they were not promoted, you can point to three specific things. And there is a separate constraint people often miss: the company may only need two directors of engineering, so the role has to exist before anyone can be promoted into it.

The book that was supposed to be half as long

Startup CXO followed Startup CEO, which Blumberg wrote with Brad Feld. Hawley is candid that there was internal resistance, because they were simultaneously starting a company, learning a marketplace business none of them had run before.

Blumberg's argument won: if the company is going to help people build cultures, publish the manual. And the underlying work would serve twice, because the same content would populate the roles inside Bolster's own product.

The process started, characteristically, on a spreadsheet capturing the skills required to succeed in each role. That fed the book, the intellectual property in the platform, and their assessments. Hawley and the CFO wrote the first sections to establish the pattern before bringing others in.

It was meant to be half the length. When they could not cut further, the solution was thinner paper, and the publisher agreed on the grounds that it is a field guide rather than something anyone reads front to back.

A layoff run as an application process

Michael's standing question produced something more useful than a wild story.

Hawley describes the conventional approach to a reorganization: a decision is made, you are told your role is changing or ending, effective immediately.

A few years ago she worked with an executive who wanted to do it differently, in a restructuring where roughly 100 people would lose their jobs while many other roles were changing shape.

They told everyone what was happening and what every job would become. Then they ran a week-long process in which people could raise their hand for the roles they wanted, say what mattered to them, or say they would rather not stay if this was the direction. The commitment was that all decisions would be made and communicated by that Friday.

The board did not agree with the approach.

The outcome was that nearly everyone who wanted to stay in the new structure did, and nearly everyone who would not have fit opted out themselves. Hawley's answer to the fear that they would lose their best people is the right one: if someone does not want to stay and leaves three months later, that was already a failure.

Her framing of why this matters is the cleanest articulation of her whole discipline. HR executes what it is told to execute. A people professional asks how to do this in the most humane way available, with the least damage to people.

Advice for joining somewhere new

For anyone taking a job, Hawley starts before the decision. Look at the leadership team and ask whether their actions match their stated values, which you cannot always determine but should try to. She adds that you have more leverage while negotiating than at any point afterward.

Once inside, relationships come first, and she recommends The First 90 Days. Set intentions for the first 30, 60 and 90 days, and let those be modest. Knowing the names of 40 colleagues and something real about each of them is a legitimate goal.

For a people or operations leader specifically, the steps are: observe for 30 to 60 days if the company allows it, understand what exists and why before changing it, fix anything genuinely broken, and then co-create three priorities for the year with the CEO.

Her word for the failure mode is the one Michael seizes on. Do not peanut butter your time across the whole company. Pick the priorities, say what they are, and tell your team explicitly what you are choosing not to do because it is important but not critical right now.

The 5 things I took away from this conversation

1. Treat people like volunteers. The reframe is small and changes everything downstream. Volunteers stay because the work matters to them and someone made sure it did. If you would not keep a volunteer with your current management, you are relying on the paycheck to do work your leadership should be doing.

2. Run the reorg as an application process. Telling people what every role will become and letting them choose, on a published timeline, is a genuinely better design than the standard approach. The result was self-selection in both directions, and it survived board skepticism.

3. Ask why 5% was ever enough. Counteroffers treat the symptom. Hawley's question, what allowed it to reach the point where a modest raise could move someone, is the one that actually tells you what is wrong.

4. Levels need two axes and a simplicity budget. What you get done and how you get it done, defined clearly enough that a peer can confirm it, and simple enough that reviews do not take hours. Their first over-engineered version is a warning worth heeding.

5. Say what you are not doing. The peanut butter point is really about credibility. A leader with three stated priorities and an explicit list of deferred items is trustworthy. A leader who claims to be working on everything is not working on anything.

FAQ

What are the strategy implementation steps for a leader joining a new company? Observe for 30 to 60 days where possible, gathering what people say and what the data shows. Understand what is in place and why before changing it. Fix anything genuinely broken. Then co-create three priorities for the year with the CEO, and communicate clearly what you are not doing so people know where your attention is going.

What does it mean to treat employees like volunteers? Assuming they have a genuine choice about staying, and behaving accordingly. In practice that means less daily instruction and more co-creating goals and work, so people show up because they helped shape what they are doing rather than because they were told to.

How do you assess a company's real culture? By asking people directly, through surveys and conversations, what they experience day to day, how colleagues treat each other, and what they love and dislike. Hawley's point is that the culture you intend and the culture you have may differ, and only the second one matters.

How should a company design career levels? Along two axes: functional skill and leadership behavior. Define what each level looks like clearly enough that a peer could confirm someone is demonstrating it, keep the process simple enough not to consume hours, and be transparent about the specific gaps between where someone is and the next level.

How do the COO and chief people officer roles fit together? Hawley sees them as natural partners covering the same operating system from two sides, one weighted toward people and one toward process. Building both at once, rather than treating culture and operations as separate projects, is where she thinks the leverage is.

Also mentioned

• Bolster, the executive talent marketplace with eight co-founders
• Startup CXO and Startup CEO, written with Matt Blumberg and Brad Feld
• Return Path, and Angela Baldonero, the chief people officer hired at around 150 employees
• DoubleClick, where Hawley moved into technology people leadership
• The First 90 Days, her recommendation for anyone starting a new role
• Jenny Lawton's episode, Hawley's Bolster colleague, on the same operating system from the other side
• Cathy Hawley on LinkedIn

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Cathy Hawley on Between Two COO's

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