On Losing Someone Great from the Team

Losing someone great from your team is a hard blow.

Hopefully when this person tells you they are moving on your initial reaction is one of excitement for them. After all, this is an all-star. She might be one of your go-to people. That means she's busted her butt day in and day out to deliver results. She is, as Drucker would say, an effective executive.

You should be proud that your work with them has helped create a new path for them. And you are.

But when you first hear them say “I’m taking a job at another company” the first thing that will happen is a sharp “oh shit” moment of emotional pain. It will be personal, and man will it hurt, especially when it’s a surprise.

Why is this? General doctrine talks about people leaving jobs for one of two reasons:

• either they’re not learning
• or they hate their manager

The questions that cycle through your head in those moments of shock will gravitate towards the second one and will largely fall into two categories: (a) how could they do this to me, and (b) what did I do wrong.

These are the wrong questions (the first because it is unfair and unhelpful, the second because this is not the time to reflect). Do not make this personal even if it feels like an emotional sucker punch right to the gut.

What you need to do is stay calm, eke out a smile (or in my case maintain a very stoic face) and probe their new gig and their reasons for leaving. Listen far more than you talk.

Congratulations, you’ve survived phase one.

So now what?

Develop a Game Plan

You need to move fast to assess their span of responsibilities and come up with a plan for who is going to step up. If there are any outward client interactions take care of those first. It’s highly likely that you’re going to have to devote more time and attention to this area for a while, but you need to move swiftly and decisively to make sure that the time you do spend here is high leverage.

In this case leverage means tapping the next star-in-waiting and helping them step up as quickly as possible. If you have someone internally this is invariably faster than looking to the outside for a solution. If it’s well-respected teammate it can also boost team morale and give that person valuable experience. This can help even if you do ultimately find a tenured exec from the outside. Internal promotions are not without their challenges of course. Whichever way you go, start the replacement process immediately.

One thing to stress here: in understanding who has the most potential you should still rely on the opinions of your soon to be ex-star manager. Just because they’re leaving doesn’t mean they don’t want to help do it gracefully. They also care about the team they are leaving behind, and you want to get a strong effort from them to set up their team for success.

Communicate quickly. Begin with those most affected, but tell everyone

Speaking of team, you should talk to the team most affected by this departure before everyone else. Ben Horowitz talks about this principle in The Hard Thing About Hard Things. Even if he applies it in the context of firing an under-performer, the same idea is true when your star leaves voluntarily. Talk to the team before gossip spreads throughout the company. But do so with a plan.

Follow up this general announcement (in person) with time for a 1:1 with these people. Don’t hide the pain. It lets people know you care.

As soon as the exec's team knows, keep moving through the circles of the company. You must be prepared to over communicate here, whether you make a move internally or externally both are fraught with potential tensions and changes to team dynamics.

Document the job to be done

Checklists, to do lists, docs to centralize all the key reports, links, files etc. Have the outgoing person document everything. The more they communicate in writing and organize their job for others the better. You should review this with them multiple times so you have context and the ability to explain it to someone else later should that be necessary. This is also a prime opportunity to see if there were any inefficiencies or processes they were handling that could be reworked or abandoned. Use this departure to optimize, not simply plug the gap.

Make time and space for yourself and the team

Make sure you give yourself time and space. Losing a star is hard emotionally, and it will be hard at work. You need to self-monitor to make sure you don’t burnout and that any moves you make to pick up the slack are well thought out and temporary.

This same level of attention and care should be given to the rest of the team. They’ll have lost someone they respect, look up to, and have a strong relationship with. They also know, probably better than you, all the details of the work they’re now going to have to own.

Preserve the relationship

At the end of the day you value your star. While they’re leaving the company, that doesn’t mean they are leaving your network. You should continue to build and nurture the relationship you have with them. Life is long. Your industry is smaller than you think. Networks matter. And this person is going through bigger changes than you are. Be there for them.

Reflect on what can be improved

Now that you have handled the triage it is time for reflection. What can you do to make sure that the team is engaged with work they find meaningful? Were there key areas of vulnerability or dependencies that you need to build greater organization redundancy for?

Finally, did you set this person up for success and continued growth? Hopefully their effectiveness had led to an ever growing trust in them which has created more exposure and higher stakes projects complete with more autonomy and a brighter and brighter career path (and more compensation). In other words, make sure that for any remaining stars you’ve taken care of “the basics.”