The Most Critical Conversation to Have With Your New Managers

The most critical conversations to have with your new managers

The crucial conversation that will get your new managers off to the right start. 

Woo hoo! You just promoted your top sales exec into the manager of the regional sales team. This should be a cakewalk right? She’s self-motivated, disciplined and organized. She’s beaten her quarterly goals for 5 quarters straight, and she knows the product inside and out.That’s why you promoted her in the first place. Now she just has to show everyone else how to sell as well as she does, and you’ll be cruising your way to those aggressive revenue goals and that big annual bonus.

If only it were that easy…

In some instances, this might work out great. In others, without the proper context and preparation, this could spectacularly fail. I know, because I’ve experienced both in my career. 🙂

The bottom line is that managing and running a team is fundamentally a different skillset and mindset than being a team’s top contributor – whether we’re talking about sales or engineering. The good news is that it is a learnable skill. The bad news is that most executives don’t take the time to properly teach someone how to successfully transition from an individual contributor to a manager.  This doesn’t mean you have to invest hours and hours of your time. A few crucial, initial conversations can be a great way to setup an ongoing dialogue that will give your newly promoted managers the best chance for success.

One of the most important things to do early on is to align expectations. A Gallup poll showed that more than 50% of people at work don’t have a clear understanding of what’s expected of them. This is an important early conversation that can set your new manager up for success and open the door for open communication as they ramp up in their new role.


The first and most important conversation you can have with your new team manager is one around expectations.  If both of you can come out of your conversation with a clear, mutual understanding around the following questions, you’ll have laid down a critical foundation that can serve as a guide they can return to again and again.

  1. What are your expectations of them?
  2. What are their expectations of themselves?
  3. What expectations should they have of their team and direct reports?

#1: What are your expectations of them? 

This doesn’t mean that you lay  out all the things you expect them to do. That’s for them to figure out. In fact, it’s better if they come up with the goals and plan for what they should be doing – they’ll feel more ownership and commitment to it because they created it. But it’s important to give them guidance in the following areas:

  • Share any executive or company wide goals that their team feeds into. For a sales team, this means knowing the topline number and potentially a range you think they need to hit. If you want to purposely keep it vague to “see what they come up with”, at least give them a sense of what a max/min might look like. For a product team, this might be the broader product roadmap and the area that you want them to own. It helps them to see the bigger picture and understand how it all fits together.
  • Share any expectations you have around communication, collaboration and reporting. Basically, how do you want to work with them? Keep you cc’ed on everything? Or only the large clients? Do you want them to try to solve problems on their own first? Come to you with buttoned up plans? Or do you like diving into the brainstorming process with them? Do you want them to email you a weekly progress report? Or are monthly in person check-ins enough? Some of these processes might be in place already – but some might change, b/c they are now overseeing a team. Be sure to communicate where you may have different expectations than before.
  • And finally, and maybe most importantly, its important to recognize that given all of the above, this is a new job for this person. One that is particularly hard to “learn” other than just jumping into it. If you can share that in spite of all your expectations, that you understand that this will be a learning process, it will pay dividends in helping them feel more comfortable with the “unknown” and potentially coming to you with feedback/advice BEFORE a disaster. 🙂

#2: What are their expectations of themselves?

This isn’t some weird trick question. Oftentimes new managers fail b/c they set extraordinarily high expectations on themselves and what they think they “should” be doing as a manager. Check out this article on common new manager worries. If you’re promoting A+ talent to management they are usually constantly pushing themselves to grow and learn and generally “be better”. This is awesome, but can sometimes backfire when it comes to management b/c of the inevitable and often visible times that they screw up.

I remember the first few months I was promoted into leading a team. Those were some of the most stressful times in my career, because I kept carrying around this notion that I should know what to do. And have all the answers. And get everything done. It took me awhile (and I’m still learning) that we can’t do it all. And that we’ll make mistakes. I remember one day, my boss came to me and said, “You look stressed.” I think I actually told him – “Well, we have so much to do!” I hadn’t realized that it was so obvious, but also couldn’t understand how he could NOT be stressed. He looked at me and said, “We do. But it will always be like this. It doesn’t help your team to see you completely stressed out.” We went on to have a great conversation about it.

What helped me was understanding that my boss was stressed too. It also helped that he shared that he knew we would never be able to get to everything. Just knowing that he didn’t expect it made me question why I would expect that of myself. I started to see where some of my expectations were unrealistic, or potentially too aggressive for what I could reasonably achieve without losing my mind. Knowing that I could actually share those thoughts with him and that he understood that we would need to make trade-offs was eye-opening.

It probably would have helped if we had talked about it earlier. 🙂 But better late than never. The big breakthrough this question can trigger is a discussion about how the expectations they set for themselves may not necessarily be your expectations for them. And that in some cases, they may be harder on themselves than needed.

#3: What expectations should they have of their team and direct reports?

This can range from – how should they think about setting goals for their teams, and how should they hold them accountable to those goals? How they should communicate their expectations to their teams? And how do the overall department and team’s goals get trickled down into each individual? This conversation isn’t about trying to nail down everyone’s OKR’s.  It’s about sharing your thoughts on how they could approach managing and leading their teams in a way that aligns with your expectations.  General guideposts and guardrails can work well here, as you want them to also really start to develop their own style as a leader of these teams. And if they need more help, check out our posts for common new manager mistakes and how to survive the first few months as a new manager.

And there you have it. If you’re efficient, you can even tackle this in your first 1:1.  An hour here, many hours saved later. 🙂

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