Keep Your People: The Startup Manager's Guide to Employee Retention

A short, practical guide to retaining employees. Focused on startups but broadly applicable to any type of company. The author has clearly been through the wringer when it comes to losing key people, which makes him a believable source of advice.

Keep Your People: The Startup Manager's Guide to Employee Retention

Highlights

There are really only six reasons that people leave companies. Let's list them in no particular order:

  1. They aren't growing fast enough.
  2. They don't have autonomy.
  3. The work doesn't fit into their lives.
  4. Compensation is an issue (they're not paid enough, or, conversely: they're paid higher than their market rate, and therefore can't leave).
  5. They have a terrible relationship with their coworkers, or more importantly: with their immediate manager.
  6. They are disillusioned with the company, or with their team's stated mission.

The important thing about this framework is that these six reasons aren't single-causal. That is: no one reason, alone, is likely to cause an employee to leave. Instead, you should think of this as six dimensions with which to evaluate flight risk. Once an employee has had 'enough', they're out of here — whatever 'enough' might mean to them.

For every new member in my team, I bring them out for coffee within a week or two of their joining, and say to them: “You won’t be with us forever, so it’s important for me to know what you want to become in the next five to ten years. This is so I can help you grow towards that goal, so that when it’s time for you to leave us, you’ll be somewhat nearer to your dreams. That’s good for you, and good for us.”

My technique works because of two underlying reasons. First, I introduce the notion that they will eventually leave the company — at the very beginning of their job with us! This is a modern-day reality, and I see no reason to pretend otherwise. Second, I implicitly communicate the terms of our working relationship. I am saying: “You are here as an employee because you believe that a job with us is a good stepping stone to grow in your career. As your manager, I represent the company in our working relationship. My promise to you is that while we make use of your skills to create business value, we will also help you grow, so that when you leave us you will be in a better position than when you first joined us.”

The next step is to construct a plan for them. Ask your subordinate to come up with a list of skills that they think they’ll need in order to achieve their dreams. Then make time to sit down and go through that list together with your subordinate. For each item on the list, ask: “how do you think this skill will help you achieve your dreams?” (If your subordinate has more than one dream, make sure to find out which dream the skill contributes towards). Then, working together, rank those skills in order of importance. Your goal here is to find a list of skills that you can turn into a concrete growth plan for them. Ideally, this plan is created with their input — though you’ll occasionally encounter a junior subordinate who doesn’t have a good notion of the skills he or she needs to succeed. In such cases, come up with a growth plan for them, based on your own experiences, explaining each of the individual skills as you go along.

The secret to good delegation is recognising that your subordinate needs to share a common understanding of the task to be done. This common understanding is what enables your subordinate to execute with full autonomy — while having the confidence of delivering a result that is acceptable to both you and the overall business. As a manager, it is your job to build this common understanding between you and your subordinates.

As in turns out, the US Army has spent decades of research looking into the art of giving clear instructions. (Which would make sense — of course they would be interested in the best way to give instructions; imagine if a battlefield commander gives insufficiently clear instructions during a firefight!) One of the early innovations they implemented was a requirement that every commander provide a ‘Commander’s Intent’ statement when issuing orders. That is: don’t just tell soldiers what to do, give them context for executing the order.

So how do you give good context around your instructions? The most concise approach is to follow Karl Weick’s recommendation for Commander’s Intent statements, originally formulated in 1983. Weick’s version asks that you include five facets in your intent statement:

  • Here’s what I think we face. (Paint the surrounding context).
  • Here’s what I think we should do. (Detail the plan).
  • Here’s why. (Give purpose). Here’s what we should keep our eye on. (Provide details, considerations, and anti-goals. e.g. “Under no circumstances should you engage with the enemy!”)
  • Now, talk to me. (Start a discussion).

As a manager, you should understand that occasionally people will leave you through no fault of your own. And you won't be able to stop them, no matter how hard you try. This isn’t a good thing or a bad thing; it simply is. However, just because you can’t prevent your people from leaving for personal reasons doesn’t mean that there’s nothing you can do about it. For starters, you should prepare for the eventual loss of any team member. That way, when you lose a subordinate to a ‘change point’ in their lives, your entire team is well prepared for their departure. In practical terms, you should do two things:

  • First, you should keep your team’s bus factor high.
  • Second, you should be extra vigilant in the lead-up to a change point in your subordinates’s lives.

Over time, I came to realise that some change points are more predictable than others. For instance, having a first child is a particularly common change point. The new parent experiences a shift in their perspective, and realises that in order to provide for his or her family, they would have to rethink their career. As a result, I’m more vigilant in the lead-up to such a change point, and I pay special attention to that subordinate in our one-on-ones after they return from maternity/ paternity leave.

If a subordinate said he wanted to learn testing, for instance, I would make sure that a good portion of our testing tasks were assigned to him. And then we would discuss his progress in the next month. Unfortunately, this monthly approach was also limited in its effectiveness. It meant that their long-term career advancement was opaque to them, because it wasn’t clear what benefits lay ahead in their future with the company — that is, beyond the plans we made for the next month.

Berkshire Hathaway vice-chairman (and famous investor) Charlie Munger has this thing he calls a ‘two-track analysis’. Munger argues that one should always apply two levels of analysis to any problem: in the first track, you consider the rational and economic factors. And then, in the second track, you consider the psychological factors that may distort the factors you’ve identified earlier. When it comes to hiring, people are influenced by pay, benefits, stock options, health care and the like. But on a psychological level, they’re influenced by the pain of self-doubt that’s so common during job searches. This leads to an intense desire to stop the job search and settle for the first acceptable offer on the table — even if it isn’t the rational thing to do. When it comes to retention, however, the math is more complex. In track one, people are influenced by their salary, their benefits package, their opportunity for advancement and their relationship with their boss. But on a psychological level, they’re influenced by inertia, by the ‘ugh field’, and by loss avoidance — the idea that if they quit this job, they might have to settle for a lousier one elsewhere. Understanding that these influences exist is the first step to being effective at both hiring and retention.

Think about plumbing services and car workshops, restaurants and hotels. It is ridiculously difficult to come up with a compelling mission for these sorts of companies — and yet they make up the bulk of our economy. But even if this weren’t the case, missions are still tricky if you’re working at a larger company. For example, imagine that you’re managing the customer service department at Google. Your team is inundated with angry customer calls on a day to day basis, as is the norm in all such large customer service operations. How are you going to retain them? By telling them they are ‘organising the world’s information?’

And that brings us back to our topic of workplace relationships. The real reason books like The First 90 Days work is that it helps people use the confirmation bias to their advantage. Author Michael D. Watkins recommends that professionals throw work/ life balance out of the window in the first 90 days of any new role; later, when bosses and peers judge you as hard-working and competent, you may cut loose a little and ride on the stickiness of their internal narratives.

There is one aspect on assigning blame that’s fairly clear cut, which is why I’ve left it to the end: never throw your subordinates under the bus. What I mean by this: under no circumstances should you ever pin the blame on your subordinate when you’re talking up, to your bosses. As a leader, you should always take the hit — even when it’s not your fault.

And yet, the primary challenge of management is to build rapport with as many members of my team as quickly as possible, within the constraints of the job.

The only point I’m making here is that making decisions around compensation are inherently political in nature. Every move you make establishes a precedence for the rest of the company. Know this: people will be watching to see what you do.

One major reason people leave companies is that they have bad relationships with their boss and with their peers. Conversely, if you have strong camaraderie with your teammates and you are managed by a fair boss, you are more likely to stay. Over the years, I’ve found that this factor acts like a stickiness multiplier. While it’s not true that ‘people leave people, not jobs’ (if you’ve read this far, you should be aware that it’s six factors, not one!) good relationships with your boss and with your peers do make a difference.