Best Employee Onboarding Process (2019)


Employee Onboarding Process

 Employee Onboarding Process (2019)

On-boarding is a very important part of the overall recruitment process. This blog explores the best Employee Onboarding Process for hiring the best talent for your business or company.


On-boarding constitutes the new employee’s first impression of the company as a member of it. The absence of a strong onboarding program can make your work environment less inclusive. 


If that impression is one of chaos, or of “we don’t care about new employees,” you can imagine the impact that will have on employee tenure. Additionally, a bad onboarding process results in new employees taking longer to become productive, which is not in your interest.


New hires who are members of the dominant group can acquire knowledge more easily from social interaction, creating a disadvantage for new hires outside this group, ultimately leading to higher attrition rates.


Let’s look at how on-boarding might evolve as your company grows. Remember that the bigger and the more mature your company, the higher the expectations are for your onboarding process.



In the first stage, your company is small and all of your employees are probably in the same office or on the same floor. On-boarding here usually starts by simply handing them a laptop and asking one of the team members to be their mentor and help them get going.


You rely on the fact that communication is still easy and that people will talk to each other anyway. But there are still some things you should do:


Ask someone to write up a brief on-boarding document, which can start with just a few notes to help orient the new hire. Then have each new hire update the document with anything that has changed or any helpful tips to pass on to the next new hire. Over time this will evolve into a fairly comprehensive guide with just a little effort from each hire.


Make it clear to the mentor that it is their responsibility to help the new hire get up to speed, and that this is part of their job expectations. Reward them with public praise and positive feedback if they do it well. Letting a new hire struggle due to lack of guidance will erode their morale quickly.


Organize a few chats with founders and senior employees who can tell the history of the company and product to the new employees. Knowing where the company has been can be very helpful in orienting new employees and explaining the current state of affairs.


Organize a few sessions wherein product teams present the most important parts of the product to new employees so that everyone understands it. These sessions should include:

  1.  Understanding the current product: why it was started, how it evolved, and plans for the future.
  2. Spending a day with the support team to understand how users perceive the product, and the most common complaints (if applicable)




After the company has grown, you might have a few teams going (up to five). If you simply add a new member to a team, they can miss a lot of knowledge about the system and could have trouble forming working relationships with the engineers outside their team. To help here, rotate new employees through each of the teams one by one.


New employees should spend one week (depending on your situation) on each team, or enough time to complete an easy task. By the end of this, they’ll have worked with nearly everybody and built personal connections, and will have a decent overview of the architecture.




The team rotation approach only works up to a certain number of teams, however. At some point, rotating through all of the teams would take too much time. And if you just choose a subset of teams, the new employee only gets limited visibility into the system.


The logical next step, then, is to create a formal onboarding program. This usually contains a part which is designed for all employees and a part which is specific to engineering/product/design.


When SoundCloud had around 20 engineers, on-boarding meant having new engineers visit several teams (around five) for one week each. As the number of teams and engineers increased, it stopped making sense to have new hires visit all of the teams. Still, there were a few teams each candidate had to visit because their area was so central to how the system operated.


One of these teams was the core API team, which was in charge of all the core business logic. Unfortunately, the constant rotations meant that the team ended up with a different team setup nearly every week. After a while, this constant churn prevented the team from working efficiently.


A Story from Duana: Rebuilding On-Boarding for SoundCloud

Our new approach to onboarding, we thought, should accommodate our increased technical and organizational complexity.


The idea was to build a structured onboarding program that provided an introduction to the complex technical architecture and introduced key members of the organization without overloading the development teams in the process.


The goal was that new engineers would be able to get up and running as quickly as possible while renewing and broadcasting the engineering culture at the same time. The culture was presented as it should be—not by misleading new hires about its current state, but by focusing on our aspirations for the future.


First approach

First, we identified the core areas in engineering and created a presentation for each of them. The presentations were given by a member of the responsible team so that new engineers would already have one contact person within each core team.


To familiarize them with the codebase and to allow them to ship something significant within their first weeks, each new engineer had to fix a bug in the mothership (the name for our monolithic Ruby application) in a one-day session, which was then deployed to production. The on-boarding took two weeks, and there were two sessions per day.


This first approach had some problems. There were too many sessions, with too much information to digest. The new engineers felt overwhelmed. After a series of bug-fixing successes, the bugs remaining in the mothership became too obscure.


It was hard to fix them, and the impact of each fix was hardly noticeable anymore. The new engineers stopped seeing the value in touching the mothership code, as they no longer felt it was relevant to their jobs.


Second approach

Second approach

The second time around, we got rid of the bug-fixing session and instead used a presentation to provide an overview of the mothership code base. We also tried to organize a mini-hackathon instead of the bug-fixing session but decided it was too much effort.


To reduce the amount of time it took to prepare and hold presentations, we considered using recorded videos, but they ended up being too impersonal; live presentations were better at putting names to faces and establishing a meaningful connection.


Instead, we changed the presentation to workshops/interactive sessions, where presenting engineers discussed the top five issues in their component, whether they were key concepts, shortcomings, or bugs. This worked much better.


Where we ended up

The first three days of on-boarding are general company presentations (legal, marketing, product, and others), attended by new employees of all departments. Following that, we do one week with one session per day about engineering topics.


SoundCloud hires engineers for a specific team, so engineers join their teams right away. Because they're an eagerness to contribute to the goals of their new teams, however, it becomes tough for engineers to focus on onboarding.


Here are the key lessons we learned:

  1. A single individual should be responsible for on-boarding, but it takes a group of people to do it well, given the effort required and the breadth of topics covered
  2. The scheduling effort should not be underestimated
  3. Attendee retrospectives and feedback are helpful
  4. Time should be allocated for process improvements


On-boarding is tremendously different when engineers are hired for a specific team than it is when they choose their teams afterward. Engineers hired for a specific team are eager to join their team as soon as possible, and as such, don’t have much patience for a broader on-boarding.


When not assigned to a team until afterward, new engineers want to learn as much as possible during on-boarding about the organization and architecture before making a decision. Hence, it is beneficial to avoid assigning teams until after the process starts.


Spotify has a much bigger team than the scope of this blog—around 600 engineers at the time we interviewed Kevin Goldsmith (who was at that time VP of consumer engineering). Still, we decided to include his very interesting on-boarding story.


A Story by Kevin Goldsmith (Spotify)

Every engineer at Spotify goes through a two week (full-time) on-boarding Bootcamp. These engineers form a temporary Squad (with the product owner, agile coach, and temporary partner engineer, called a “buddy”) to learn the general setup and engineering approaches, such as build processes. The first two days are general introductions (company, product), then the engineer works on a product feature.


In the beginning, it was difficult to motivate product owners to spend two weeks on-boarding, but after a while, the product owners realized this amounted to getting an extra team for free. Product owners then started competing to get the new squad.


Each squad so far has shipped one feature to production.




One approach that can be used either alone or in combination with other onboarding approaches is a mentor or “buddy” program, which gives the new hire a specific person to help guide them during their early days at the company.


According to the article “Buddy System 101: New Employee Onboarding and the Benefits of the Buddy System”:


A buddy is a colleague—not a manager or supervisor—who is assigned to a new-hire for the first few months of employment and who acts as a guide for the day-to-day activities of the company.


A buddy is someone who can be available to show the new-hire around the office, go over protocols and policies, and generally help familiarize him or her with the company's inner workings and culture.


Because of this, we recommend assigning a “buddy” to each new employee —someone to help ensure the new employee finds the coffee machine, knows where people have lunch, and so on.


And as mentioned earlier, it’s important that mentors know the expectations of their role, and get rewarded when they do it well. This can also be a great first step toward leadership for a young team member, to see if they have an aptitude for helping others be more effective in their jobs.



Off-boarding is about more than getting employees’ hardware back and closing all their accounts. It’s more important to learn the causes for their departure and gather feedback on how the company can improve by performing exit interviews. Ideally, the answers you get from the employee are unsurprising, since the manager and HR have already discussed these with the employee.


If they regularly reveal completely new things, it may mean something has gone horribly wrong earlier in the process (e.g., the manager hasn’t performed 1-on-1s or hasn’t acted on feedback the employee had given). If things are working well, there should be no surprises.


Pay attention to which departments are experiencing attrition. If certain parts of the organization lose more people than others, you should definitely take a look at the reasons. There are some common patterns in fast-growing start-ups with regard to attrition:


  1. The culture has changed (e.g., from being a collaborative environment to more of a competitive one)
  2. Employees feel there is little possibility for career advancement


The company is scaling poorly in one or more dimensions. Look at the “Warning Signs” compilation in the final blog to see if one of these signs align with the feedback from the employee.




When an employee resigns, many companies will classify the resignation as one of two types: regretted or non-regretted attrition.


When the attrition is regretted, it means the company would prefer that the employee remains on the team. This often triggers an attempt to “save” the employee through conversations with HR and senior leaders.


These should reveal the reasons behind the resignation, which should be tracked by HR to understand any problems that need to be addressed. Make sure you consider these points:


  1. Did the manager listen to the person’s concerns? Does the person feel treated fairly by the manager?
  2. Was it merely a compensation issue?
  3. Did the employee feel there was a culture problem? If so, you need to determine whether this is because the culture changed in a way the employee didn’t like, or because the culture of the company was not what was promised.

Especially in the latter case, you should look at what you communicate during the recruitment process.


In the case of non-regretted attrition, the company is willing or eager to let the employee leave. A typical scenario is that the employee received some critical feedback or was put on a performance improvement plan (PIP) and decided to leave as a result. In this case, make sure you consider:


  1. Do you need to improve the recruitment process? Is there a flaw in it that is keeping you from learning crucial information?
  2. Was the employee only a good fit during an earlier stage of the company? If so, this is pretty normal and not necessarily cause for concern.


Tracking these separately can help clarify whether a surge in attrition is due to solid management (e.g., “managing out” poor performers), or a management failure of some kind.


But make sure that the classification isn’t left solely to the manager. When someone decides to leave, there is a strong temptation to say “Well, we didn’t want that person anyway.” This artificially inflates the non-regretted numbers and can mask the real reason for the departure.


In all cases, it is worth doing a thorough exit interview, because often the reasons cited by the employee are not the actual reasons they are leaving. It’s much easier to say “I’m just looking for new challenges” than to say, “I think my boss doesn’t like me.”



You should work on minimizing all forms of bias throughout the process, from the initial presentation of candidates through to recruitment and onboarding. Try to establish a transparent, consistent interview process in order to:


Mitigate the fast-tracking of referrals, making sure that referrals are interviewed consistently with other candidates and not given preferential treatment


Ensure referral feedback is handled appropriately, as another data point but not as an override for any interviewer concerns


Make sure job postings are inclusive and avoid gender-biased language. One option is to ask underrepresented groups internally to review job descriptions before they go live.


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.


Regularly remind the team to be aware of unconscious bias before they leave feedback and call out stereotypical evaluation/feedback not based on merits, but rather on differences (i.e., “lack of presence” for female candidates, “communication skills” for underrepresented minorities, etc.).


To create awareness, we recommend you conduct an unconscious bias training with recruiters and recruitment managers.


A recruiter with strong EQ and experience running high-quality, rigorous interview processes will do a lot of these things naturally, but it is also a good idea to bring someone in who specializes in this area to take a look at your process early on before you develop bad habits.


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.


Because many underrepresented groups make up an even smaller percentage of senior candidates, consider taking headcount out of the equation.


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.




Reference checks are basically the validation of your internal process and an important chance to catch problems before they slip through. To see if your impression of a candidate matches their performance at a previous job, you must talk to their former coworkers.


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.


Be aware that candidates tend to list people who will speak positively about them. Try to get a 360-degree view by asking the candidate for references from people who worked above them, alongside them, and beneath them.


Don’t try to merely confirm your impression of the candidate by asking leading or shallow questions. As one colleague described, “The typical call I get lasts five minutes with the reference checker basically saying, ‘We adore this candidate. You love ‘em, too, right?’


They make the call hoping I won’t say anything that will cause concern about the candidate which would throttle their company back to square one of the recruitment process.”


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?”.


Prefer to talk to references over the phone when you have the opportunity; people are often less open when asked to respond in writing (for legal reasons or otherwise). Be aware, however, of country-specific legal requirements (in Germany, for example, a written reference has to be benevolent).


It’s likely that speaking to references will confirm that you made a great decision. But what happens if the references raised concerns? What if they were negative?


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.


You’ve interviewed a great candidate and decided to make them an offer to join your team. Successfully closing a new hire, especially in a competitive market, requires a clear and compelling offer, presented the right way. It’s important that you:

  1. Make sure the candidate understands their future role at the company.
  2. Set clear expectations for the candidate’s first few months at the company.


Make sure the candidate understands the financial aspects of the offer, especially any elements beyond the base salary. Bonuses and equity can be very difficult to understand, and candidates will appreciate any clarity you can provide.


If you’re successful in convincing the candidate to join your team, the next step is to onboard them. Onboarding is the process of providing your new hires with the detailed knowledge they need to be a happy and productive employee and is often an overlooked part of the recruitment process.


In addition to closing and on-boarding, we will also cover off-boarding which, when done well, provides a great opportunity to improve your recruitment process and your work environment. We will also cover acquihires, as there are some important considerations to address when merging an entire team into your own.


People Management:

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

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:

  1. Ensure the right technical decisions are being made by the team.
  2. Ensure projects are tracked accurately and shipped on time.
  3. 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:


  1. Adding the wrong people to the team, or allowing the wrong people to stay on the team too long before taking action
  2. Letting the team’s morale and productivity suffer by ignoring members’ work assignments, compensation, and career growth
  3. Providing no focus or prioritization, and allowing disputes and distractions to hurt productivity
  4. 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.



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

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:


Early stage

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.


Transition stage

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.


Mature stage

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 ???.



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.


  1. Warning signs that people management is needed
  2. 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:

  1. The founders’ previous management experience
  2. The more they have, the longer they can get by with ad-hoc management without accruing too much management debt.
  3. 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.


Growth rate

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

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.


Cultural opposition

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.


Lightweight learning

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.


Professional coaching


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.


Reading group

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.