This week is Part 2 of a multi-pronged question about transition management. Our reader asked about:

  • Keeping people invested in a project when it’s winding down
  • Managing when the work isn’t fun or glamorous or cutting edge
  • Knowing what to say and do when people on your team are exploring different companies
  • And also, what do you do when you’re the manager and are in the same boat?

We’re tackling numbers two and especially three today. Read the full question and Part 1 here.

Emma: I think the most powerful way you can be a good manager during transitional times is to be an honest, invested, and available resource to people who are trying to figure out what to do next. Career counseling is one of the most supportive manager moves.

Andy: It’s also pretty tricky. Talking honestly with someone about (maybe) leaving your team is sensitive and requires objectivity, which, as a person’s boss, is hard to have.

Emma: We’ve mentioned before how attrition is healthy for a business, and I was lucky that, at one of my first jobs, I was exposed to really great managers who were actively involved in helping their people make confident career decisions. I remember seeing one of my favorite managers, Stephanie, counsel a photo editor into an entirely divergent career path — I’m talking completely out of the organization. I couldn’t believe it. You’re helping someone leave the company? …isn’t that bad?

Andy: At a glance it sure seems like it. Hiring and training is expensive and hard and now we’re helping people leave?

Emma: I flat-out yearn for that kind of commitment and care from the person in charge of my worklife. When it comes down to it, yes: You need butts in seats doing the work. But you also need people who aren’t miserable or mad about what they’re doing all day.

Andy: And, honestly, there’s no way to stop a wandering eye, especially during a time of big transition. My only option as a boss is to be direct and honest about what my team, my company, my projects, and I have to offer. If I share all that, and someone is still intrigued by the outside world, I’ve found that the best route is to have them go explore it. I try to think of it like Rumspringa. Of course I want my person to stay if they want to stay. But it’s powerful to be okay with them figuring out what’s best for them.

Emma: Broaching the subject of career Rumspringa can be awkward — it takes a lot of trust and transparency. But those are the ingredients for a truly delicious 1-on-1. I recommend something like:

“This project is winding down and I know how destabilizing that can be. How are you feeling about what’s coming next?”

Andy: I love how that opens the door to a conversation about next steps. If you get a wishy-washy answer — “Oh, fine, you know…” you can probe gently to see if they will open up a bit:

“Totally. Do you have any questions or concerns I can shed some light on?”

Still nothing? Let it be and surface it again in your next 1-on-1. But if they bite, dig deeper.

Emma: One way to be supportive of someone who feels in flux is to help them get clear on what hole they are hoping to fill by hopping jobs. Human beings are terrible at knowing what they want, let alone putting language to it. I’m terrible at it.

Andy: I am too, and without that soul searching, the Different = Better mindset will always win. Therapists have borrowed a term from Alcoholics Anonymous for this: pulling a geographic. If something’s not going well, move to a new place and everything will be better!

Unfortunately, wherever you go, there you are. Which isn’t to say moving can’t be awesome, or that switching jobs won’t lead to great things.

Emma: Agreed. I’ve hopped a lot of jobs with very few regrets.

Andy: Knowing what you want is pure, unadulterated information. If you’re clear on that, it gets way easier to evaluate new offers that come along.

How to Know What You Want

One way to know if a new job actually has greener grass is to evaluate how it aligns with your values — the stuff that’s most important to your happiness. Everyone has values. Lots of people have no idea what theirs are. This exercise will help. (Note: This is adapted from Miller, de Baca, Matthews, and Wilbourne’s Personal Values Card Sort. We also found this Mind Tools article useful.)

Identify Your Top 10 Values

This list has 63 common values to get you started. Print them out as cards. It’s nice to stack piles of Yes! and ?? and Ew No, or to order them from Must Have to Couldn’t Care Less to Don’t Want. Not seeing something critical to your job fulfillment? Add it in.

Being a leader
Being challenged
Being entertained
Being the best
Continuous improvement
Feeling connected
Health care
Leave policies
Office perks
Open communication
Personal expression
Personal impact
Physical work
Social impact
Work travel
Working conditions


Struggling to identify which values are most important? Ask:

When have you been happiest? Proudest? Most content? Least stressed?

  • What were you doing?
  • Who were you doing it with?
  • What about it made you feel that way?

Then flip the questions: When have you been the most miserable? Complained a lot? Lost sleep? Dreaded Monday mornings?

If Possible, Follow Up in a 1-on-1

This is where the really juicy discussion comes in. Start with a big broad question to open the conversation:

“How’d that values exercise go?”

If your report is willing to share their top 10, remember that different people interpret values in different ways — one person’s influence is another person’s autonomy or control — and we’re all susceptible to values we think we should have as opposed to the ones we actually have. “Tell me more” sentences are good and safe to use:

“I’d love to hear more about what spontaneity means to you.”

And while this exercise is less about debating vocab than identifying feelings, as their manager, you have unique perspective you can share. Tell the truth with some tenderness:

“Ooo, spontaneity! I wouldn’t have guessed it would be a top pick for you. What kind of spontaneity do you value? When unplanned assignments pop up are you more frustrated or excited? It’s OK if it feels like something you’re supposed to value, but maybe don’t actually like — that’s how I feel about ambiguity.”

Be Direct About How You Can Deliver on Those Values

This is where you can either make a case for staying put on your team, or confirm that another company might ultimately be a better fit. You have a few options.

When you want them to stay, and have the power to make changes or offer more:

Mirror back what you’ve heard. Ask questions about how they see their current job meeting and missing those marks. Describe what you’d like to do and what that will look like in reality.

Often this will be more money, more responsibility, a different title, better perks. You’re going to need backing from your boss (and their boss) on any changes so it’s got to be worth it: top performers, lynchpin teammates, critical skill sets.

“I hear that it’s This Value and That Value that really matter for you and I want to do what I can. I really want to keep you on the team for These Specific Reasons. Here’s what I can offer, and the timeline I can make it happen.”

Be careful not to overpromise — it’s a quick way to destroy trust. If you feel the urge, add a qualifying start like, “I wish I could snap my fingers and promote you tomorrow…” It’s a nice way to clear your throat from actually saying you’ll do the impossible.

When you want them to stay, but can’t (or don’t want to) offer more:

Reinforce that you value their position on the team, and describe how you believe their role as-is meets their values. This might include recasting some of the current work in light of their future goals, or attaching those types of opportunities to them. It may also be reminding them of advantages they have that they’re not currently using. In this situation your mission is to show them how green the current grass actually is.

“I really appreciate the work you do on this team, and I want you to stay here. From everything we’ve discussed, I think this is a really good fit for where you’re at and where you want to go in the future. Here’s why.”

“I’m hearing that flexibility is one of the most important things to you. Have you considered taking more advantage of our work-from-home policy?”

When you agree they should move on:

Be honest with the limits of the role or the organization you’re in and admit if you can’t deliver on what they want. Remember, there’s huge impressive strength in showing your team that you’re on their side. Yes, you’re also on the company’s side, but in the long term, those two goals are the same thing.

“I hate to lose you, but I think you’re right: this other opportunity sounds like exactly what you’re looking for — and we can’t match it.”



Andy: We have one caveat to this whole career counsel conversation: Your report is the ultimate arbiter of their career path. You can act as a coach and a resource, but you aren’t their partner in this.

Emma: Or their parent.

Andy: You are still currently their boss. I think it’s helpful to remind direct reports that there is such a thing as sharing too much.

Emma: The target you’re aiming for is open, but not overly open; honest and direct but not threatening. It’s really pro-level managerial stuff you’re dealing with.

Andy: Good luck and let us know how it goes!

Good Boss Achievement Stickers: Career Rumspringa Edition