Ensure referral feedback is handled appropriately, as another data point but not as an override for any interviewer concerns
The editing process can help recruiting/ leadership to learn some of the basics about what is considered gender neutral and attractive to a wider talent pool.
A headcount policy, for example— wherein each manager has a certain number of reports and wants to maintain that number—can cause teams to focus only on candidates with more experience.
If your overall headcount allows some flexibility, you can state that new hires with the less overall experience and from an underrepresented group don’t count against the headcount of that specific team.
This is usually the last step of the interview process; references are usually busy people, so it’s important to only interrupt them once it becomes truly necessary. Reference checks should be mandatory for managers and optional for individual contributors.
Instead, clearly, explain the position you’re recruitment for to the reference and then ask concrete questions, such as: “Do you think X is a good candidate for this position?” and “Why is X no longer with the company?”.
We recommend discussing the results of the reference calls with the other decision makers in your recruitment process so the group can then decide whether or not to change their decision.
For many fast-growing companies, introducing a management role feels, at best, like a waste of time, or at worst, like the beginning of big company ills: more meetings, slower decision making, political maneuvering. You can almost hear the protests of early employees ringing in the hallway: “We’re going corporate!”
But despite the potential objections, an explicit focus on people management is vital to company success, particularly at fast-growing companies.
With proper training and a healthy culture, people managers can help teams scale by maintaining morale, ensuring alignment between work assignments and company goals, resolving disputes, and preparing the engineering team for the next phases of growth.
Consider these problematic scenarios:
“At one point, my manager had up to 70 reports. Our feedback meetings were worse than useless. He basically cut-and-pasted my self-review with a few quotes from what my teammates had said about me...”
“I’ve been at the company for six months and already I’ve had three desks and four managers. I’m actually not sure where my manager’s desk is any-more.”
“On my first day, I was issued my laptop and badge by IT and then told to go to my manager’s office. I wandered around until I found it, but she wasn’t there. I waited in the hallway for two hours. Luckily, some former co-workers from my previous job found me and took me to lunch.”
Any veteran of a fast-growing team can relay similar stories. Are these negative experiences just par for the course? The cost of doing business in tech? On the contrary, we believe an informed approach to scaling people management can avoid such missteps and materially improve the performance of your team and company.
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Understanding People Management
When new teams are formed, whether as a startup company or within a larger organization, the early days feel wonderfully efficient. Brainstorming ideas, hashing out a design, fixing problems—it all feels effortless.
The hard work and long hours don’t feel like a burden, because the impact of the work is clear and meaningful. The team builds a bond forged by the challenges they are tackling together and the uncertain road ahead.
If they are successful in building the right product, the team often falls victim to its own success. Overwhelmed by the demands of a flood of new customers, the already hard-working team finds that they cannot keep up.
The only option to quickly scale the team’s output is to grow the team. The first three blogs covered the mechanics of growing the team and how those mechanics change at different scaling points.
Remember, teams, are groups of people. Because people are unique in their collection of talents and motivations, it’s rare that they can self-organize into a cohesive unit that can efficiently pursue a common goal. This is the key role that people managers play.
People management is distinct from other management responsibilities:
Ensure the right technical decisions are being made by the team.
Ensure projects are tracked accurately and shipped on time.
Ensure the right product is being built for the customer.
These are important responsibilities, and at many companies, the same managers may be responsible for some of these in addition to people management. But they are less critical to scaling than having a people management strategy that helps each team grow more efficiently and effectively.
As my colleague, Joe Xavier once said, “People management provides the structure and connective tissue to allow a group to achieve a common objective.” Successful people managers achieve this by:
Getting the right people on the team, and getting the wrong people off the team Ensuring the team is happy and productive by providing motivating work assignments, appropriate compensation, learning opportunities, and career guidance
Helping the team succeed in their work by focusing on the highest-priority outcomes, resolving disputes and deadlocked decisions, and removing distractions Providing the team with any necessary resources, whether these are new team members that can fill a skill gap, conference room space for a brain-storming session, or a big monitor to display a project dashboard
These are the critical functions of people management. Though the specific practices involved may vary quite a bit, these functions apply whether the team is large or small, junior or veteran, composed of individual contributors or senior directors of large organizations.
However, if you flip that list around, it’s easy to understand how a lack of investment in people management can harm the growth of the team by:
Adding the wrong people to the team, or allowing the wrong people to stay on the team too long before taking action
Letting the team’s morale and productivity suffer by ignoring members’ work assignments, compensation, and career growth
Providing no focus or prioritization, and allowing disputes and distractions to hurt productivity
Starving the team of the resources they need to be successful
Those of us who have lived through periods of hyper-growth will recognize many of these problems and can tell tales of the resulting damaging effects: burnout, team conflict, a loss of faith in leadership, confusion about the team’s mission, and ultimately unwanted departures from the company.
For an interesting case study in the value of people management, read Buffer’s revealing retrospective on what happened after they eliminated managers and why they reverted eight months later.
FROM AD-HOC TO FORMAL
At small companies, people management functions tend to be handled as needed by individuals in leadership positions—typically, the founders of the team.
You see examples of this everywhere in the tech startup landscape, such as the common pattern of having the first dozen or so engineers report to a founder-CTO who has little or no management experience. This mode is a form of ad-hoc management.
People management essentials
If your team is currently operating in an ad-hoc management mode, there are a few essential things you should be doing, even before you think about growing the team. Everyone on the team should know who they report to (i.e., who their manager is). The only exception is the CEO, whose “manager” is the board of directors.
Everyone should have a regular 1-on-1 meeting with their manager.
During this 1-on-1, they and their manager should discuss the fundamental aspects of their job—in addition to asking whether they know what’s expected of them, if they have the resources to do their job, and if is there anything blocking them from making progress, their manager should also provide feedback on how they are performing and give suggestions on how they can improve.
Managers should understand the career aspirations of their team members, and strive to provide them with challenges and opportunities that help them move in that direction.
Without these fundamentals in place, most teams have no hope of scaling successfully. A complete tutorial in the basics of people management is outside the scope of this blog, but there are numerous resources available.
Dealing with growth
As the team grows larger, this mode starts to break down. A founder–CTO may find that after a week full of VC pitch meetings, partner negotiations, and architecture debates, they have no time to schedule 1-on-1s, provide feedback, or resolve personal conflicts.
Or they may feel less qualified to deal with these as the team grows and people management tasks become more complex.
Or a crisis may erupt: say a key employee quits due to lack of a clear career path or an unresolved conflict with another employee. Whatever the circumstances, the leaders of growing teams at some point realize they need to transition to an explicit management structure and culture, or more succinctly: formal management.
The timing and method of transition from ad-hoc to formal management varies from team to team based on many factors. Despite this, there is a common path of how a company scales its people management:
This is when ad-hoc people management starts. A team of 5 to 25 people (roughly half working on product development) forms around a handful of founders and one founder acts as the de-facto people manager while the team builds its product and searches for a market and business model.
During rapid growth, the team finds a market and starts to grow quickly from 25 to 100. The ad-hoc people management approach starts to break down. The leadership team begins to formalize management roles and transition or hire individuals into those roles.
The company now has formal people management at scale. The initial management team continues to grow and evolve as the company grows from 100 to several hundred employees.
An approach to multi-layer management (e.g., VPs and Directors) is put in place, as are more complex systems for performance management, career growth, and so on.
It’s important to distinguish the reporting structure at a company (i.e., who reports to whom) from the organizational structure (i.e., how individuals are organized into teams to get things done).
These often overlap, but not always. And in matrix organizations, all the ICs in a particular discipline (designers, frontend engineers, backend engineers, PMs) report to a manager for that discipline, but they get distributed into cross-functional teams to tackle specific projects. We’ll cover the various options in more detail in ???.
WHEN TO FORMALIZE PEOPLE MANAGEMENT
As you enter the transition stage, it can be hard to know when the timing is right for introducing formal people management. Leaders, distracted by the customer and team growth, often rely on gut and intuition, or simply wait until a crisis emerges to force the issue. But there are usually early warning signs that people management is needed. Recognizing these and taking action can help avoid a crisis.
Warning signs that people management is needed
There are a number of warning signs that suggest a move from ad-hoc to formal people management is needed:
Failed 1-on-1 meetings
Team leaders no longer have time for 1-on-1 meetings. They may be too busy putting out fires and doing “real work” to meet with the team.
Or perhaps they spend too much time on 1-on-1 meetings. Because of urgent personal issues, team leaders are failing at other critical tasks like strategic planning and fundraising.
Confusion about the direction of the work and team
Team members become bogged down in disputes about the path forward or confusion about priorities and increasingly need leaders to step in and make decisions to unblock progress.
Declining product quality and productivity
Product quality is slipping—there are more bugs, customer complaints, downtime, and rollbacks. Or team leaders feel that engineering productivity is slipping and wonder whether the team is working hard enough or getting distracted by non-essential tasks.
The conflict between groups or individuals
You might hear “We couldn’t hit our milestone because Team X failed to adequately support us.” Or you might notice a lack of collaboration between certain groups.
Morale trending lower, attrition trending higher
Team members see increasing examples of poor morale—grouchy emails, antisocial behavior, and cynical talk around the water cooler. A noticeable shift to later arrival times, earlier departure times, or more frequent last-minute “work from home” days.
More talk of “I’m not progressing in my career” or “The work isn’t interesting anymore” or “I’m feeling burned out.” And employees are leaving the company at a noticeable rate.
Individually, none of these warning signs necessarily indicate a crisis. But if you’re seeing several crops up at your company, it’s time to act. Try to quickly diagnose the underlying causes, and in parallel start working on a more formal approach to management. The next section, Introducing Formal People Manage-ment to a Team, describes how to do this.
At first, you might just look at the size of the team. There is a body of research on how many direct reports a single manager can reasonably handle, often called span of control, with typical numbers quoted in the 7 to 10 range. Based on this model, when the founding team grows beyond 10 people, it’s time to move to a more formal management structure.
But different teams require different levels of teaching and assistance from their managers, something Drucker calls span of management responsibility. Some leaders are more equipped than others to perform ad-hoc management tasks in parallel with their other tasks.
And some team structures allow day-to-day management tasks to be distributed across multiple leaders instead of being centralized in a single people manager. So there is no simple rule for when to shift to formal people management.
There are some obvious factors to assess in planning the timing of your transition to formal management:
The founders’ previous management experience
The more they have, the longer they can get by with ad-hoc management without accruing too much management debt.
The maturity of the engineering team
This is not simply “years of experience” (although it doesn’t hurt if your engineers have worked for a significant time at well-managed companies). But some engineers are simply more self-managing than others, requiring less time and input from their manager to get their job done, and less coaching on how to improve.
The team’s familiarity with each other
A group that has worked together successfully in the past may need less management than a collection of individuals who are still learning about each other’s strengths and idiosyncrasies.
The team’s decision-making ability
Some teams are able to act independently, while others require input from founders/leaders to approve their decisions or break ties.
Teams that need to grow quickly will get the most benefit from a dedicated people manager since they can drive sourcing, organize the interview process, onboard new engineers, and ensure that they have appropriate work assignments.
Importance of execution versus exploration
If you’re staring at hard deadlines and shrinking market windows, formal management can help improve predictability by reducing churn and duplicated effort. But it can also reduce exploration and serendipity as managers attempt to focus the team on the current strategic plan.
Ultimately, it comes down to how much people management the team needs, and how well such management is getting done in the absence of an explicit manager.
Delaying Formal Management
When is appropriate to delay the transition to formal management? In some situations, particularly if none of the warning signs above are evident, waiting makes sense. But we have also seen many cases where a delay is motivated more by fear or inertia than by logic or experience. For example:
Past bad experiences with management
Leaders who have suffered under bad managers in the past may feel that the role is more harmful than helpful. While this is understandable, consulting with investors, board members, and/or mentors should quickly dispel this misconception.
Sometimes a predisposition against people management is more philosophical, based on a desire to elevate the role of the individual contributor on the team.
Many startups tout the virtues of their “flat org structure,” which may be based on a misunderstanding of the value of good managers, fear of the cost of recruitment bad managers, or a presumed inability to distinguish between the two.
These reasons, though understandable, are more likely to lead to an accumulation of management debt than to result in a novel new way of managing and scaling teams.
That said, there are sometimes valid reasons to delay, particularly when the leadership team needs to balance the cost and risk of making the transition against major company events.
As this blog should make clear, introducing formal management is not a trivial exercise. Hiring dedicated managers or converting individual contributors to managers both have financial costs in the form of salary and benefits.
There are also execution costs in the time and mental focus required to make the transition, particularly from the leadership team. Funding constraints or critical events like a product launch or fundraising may be valid reasons for leaders to delay incurring these costs.
Being managed as a manager
The way an IC is managed and the way a manager is managed can be very different. As a manager-of-managers, explain how you intend to provide direction, define goals, and set expectations.
Also, try to be clear about where you are comfortable with autonomy and where you expect to be involved in decision making. If this is your first time managing managers, you may not be clear on these yourself, so seek some guidance from a mentor or company advisor if you need it.
Preparing the team with a new manager
We covered much of this topic in the section on Communication and Rollout of a formal management structure. In short, be transparent about why this person is becoming a manager, how their success will be evaluated, and what changes the team should expect day to day if any. Do this before the reporting relationships change so that any concerns can be surfaced and dealt with prior to the transition.
It would be nice to be able to say, “Sign your new managers up for this 12-week class and they’ll be totally set up for success!” But it’s unlikely such a class exists, nor is it reasonable for every organization to lose people for 12 weeks to get them ready for their new role. But there are simple, time-efficient things you can do to help educate a new manager on the basic parts of their new role.
The simplest approach is to pick a specific management blog, book, or article that you find particularly relevant. Ask the prospective manager to read it and then have a one-hour discussion with you when they are done.
It doesn’t really matter which one it is, as long as it is broad enough to cover some essential management skills (e.g., 1-on-1s, providing feedback, and setting direction). The goal of your follow-up conversation is to ensure that you both have a shared understanding of the role and your expectations of it.
It’s not uncommon for two managers to have very different styles of management, so this is your chance to establish which aspects you want to be done a certain way, and which ones the new manager is free to define on their own.
For example, you may feel strongly that managers must provide informal performance feedback to each report at least monthly, but care less about how the rest of their 1-on-1 meetings are structured. Not establishing these “invariants” up front can lead to friction between you and the new manager down the road.
If you have the time and motivation to do more to prepare your new manager, pick a few ideas from this menu and run with them:
Ask a few managers you know, either in the company or outside the company, to meet for 30–60 minutes (perhaps weekly for a month) and talk about their transition, what they wished they had known before starting the job, or the biggest challenges they’ve faced.
There are lots of executive coaches out there, not all of them great. But if you know a great one, or can get a referral from your network, the money you spend on this will probably be repaid many times over.
This is a great way to foster ongoing learning in your management team, and there’s no reason why a prospective manager couldn’t join the discussion before their transition.
Focused practice sessions
Use part of your 1-on-1 time to practice the skills you think will be most difficult for your new manager. For example, “Imagine that I report to you, and I’ve been working for several months leading a project with an important client.
You’ve decided that my job performance isn’t up to snuff and have decided to replace me as the lead with one of my peers. Take a few minutes to think about how you’d break the news to me. Then go ahead and try it.”
Have your new manager shadow you in all your meetings (except perhaps 1-on-1s) to get a better sense of a day in the life of a manager.
Especially useful in areas where the new manager has had little or no visibility, such as recruiting and closing candidates, presenting to upper management, collaborating with other senior leaders, or the legal obligations that managers have regarding harassment and hostile work environments.
Whichever of these you go with, please remember the most important thing at this stage is not adopting any specific training technique, but fostering the habit of ongoing education, which is so easy to lose track of during the confusing and busy early days as a manager.
This is not a promotion
When converting an engineer to a manager, make sure you don’t describe this as a promotion, but rather a significant change in role and responsibilities.
There are two motivations for this rule. First, you don’t want engineers to think that shifting to management is the best way to get ahead since this is not a healthy motivation for taking on such a different and challenging role.
Second, describing the conversion as a promotion and/or showering the person with fanfare will make it very difficult to step back from the role if they decide it is not for them.
If a new manager ends up failing or unhappy in their new role, you don’t want them to have any artificial incentives to stay in that role. Better that they step aside and get some training if they want to try it again someday. Lindsay Holmwood wrote an excellent post on this subject titled, “It’s Not a Promotion, It’s a Career Change”.
A common approach that we strongly endorse is giving an internal candidate an incrementally increasing amount of management responsibility to assess whether she would enjoy this new role or not. For example, you may have a promising potential manager who is acting technical lead for one of your teams.
Before making the role change official, you could first ask the tech lead to take a larger role in career guidance for the team members by having her own 1-on-1 meetings with them, perhaps alternating with your own to avoid meeting overload.
Then, have her take on more of the team roadmap planning and customer outreach. And then have her present the roadmap to key stakeholders. At each step, you have an opportunity to assess, provide guidance, and gather feedback from them on whether these responsibilities are appealing or a burden.
New managers, as with any other employees, should know when and how their performance will be assessed and communicated. Of course, continuous timely feedback is best, but you should also agree on a milestone for a more formal assessment.
This is particularly helpful for new managers because, frankly, not everyone is cut out to be a manager, nor will everyone enjoy the new role. Without a mutually agreed upon the date on the calendar for a go/no-go decision, it’s easy for months and months to pass without making the difficult decision to revert.
Make sure when you pick the date, perhaps three or six months out, that you also provide the rubric that you’ll be using to assess them. Will it be solely your view, or will you solicit 360 feedback?
What aspects of the role will you be looking at? This provides some structure that the new manager can use to guide his own development and do his own self-assessment. Additional guidance on how to help managers thrive is covered in the section on People Management at Scale.