How To Talk To Your Boss (or your team member) About Getting Promoted When It’s Uncomfortable

As an executive coach, I’ve spent nearly 20 years working with highly successful leaders who’ve hit a bump in the road. My job is to help them get over that bump by clarifying their goals and figuring out a way to reach them so that hopefully they can lead with a little more ease.?

I work with some of these leaders on my Harvard Business Review Presents?Coaching Real Leaders podcast, where I take you behind the closed doors of real coaching sessions. I also host the?Coaching Real Leaders Community, where I’m joined by an amazing group of leaders and coaches who come together to take a deeper dive into CRL episodes and their career issues.?

And in my?Coaching Real Leaders?newsletter, I share takeaways from the many coaching conversations I’ve had over the years. Whether you are a coach or a leader, my hope is that this will help you more easily navigate the challenges you and/or those you coach face.?

On my latest Coaching Real Leaders podcast episode, “How Do I Get Promoted Without A Clear Path?”, my guest coaching client is Sam, a mid-level finance professional who wants to get to the next level. But he says doesn’t know how because his manager has not given him any feedback beyond “Just keep doing what you’re doing.” By the end of my coaching session with Sam, he recognizes what he needs to do to move forward and one of his action steps is having a follow up conversation with his manager to advocate for himself.

But what didn’t fully make it into the final episode (and made for a lively discussion topic during the live episode debrief with my Coaching Real Leaders Community yesterday) is how difficult it can be to discuss your career progression with a manager who’s been vague from the get-go. As a result, so many of us in similar situations as Sam avoid the conversation altogether landing us right back to where we already are – with no clarity. And, as one of the CRL Community members pointed out, these conversations can also be quite uncomfortable for the boss as well! So, to figure out how to have a productive discussion with your boss (or vice versa), I turned to my trusted colleague and dear friend, Amy Gallo, whose mission is to help people experience less stress in their interactions with colleagues and feel more confident navigating uncomfortable situations.

Amy had listened to the episode, so I was curious what suggestions she had for Sam and those struggling to have a conversation with their boss about future career opportunities. Here’s what she shared:

Oftentimes we hesitate to advocate for ourselves because we imagine that conversation will feel like a conflict - you're advocating for something that the other person doesn't want to give. But that's often not the case. My advice for Sam - and for anyone who wants to increase their visibility, advocate for themselves, and even gain clarity from their boss - is to drop the "difficult conversation" framing and think of the conversation as a collaboration. You and the other person have a shared goal - to achieve your success. And I would even say that goal out loud. Sam might also want to make his intention clear. He can start the conversation by saying, "My intention here is to explain what I'd like to achieve in my career and to get clarity from you about what I need to do that." Making that simple and clear statement upfront will help frame the conversation. ?Sam still might not get the answers he wants from his boss but at least he's done his part in being direct and asking for what he wants.

But if you are not used to asking for what you want, it can be especially challenging to do so with your boss. I was interested in Amy’s thoughts on how to make the ask when it’s not something you’re comfortable doing as was the case for Sam. ?

One thing that Sam might try is to not just talk in terms of what he wants from his career but the impact he can make on the organization. It could help his boss get on board with that goal if they know why Sam believes reaching this goal will help the company and what they're trying to achieve. What impact does he want to make? How will he push the company forward if and when he takes on that new role?

Once of the nuances about this episode is that I did not have access to Sam’s manager to gauge ?his perspective on Sam as I typically would over the course of a coaching engagement. Could it be that the manager was also avoiding the conversation because he did not want to discourage Sam? I’m not sure if that was the case but it is a dynamic that often surfaces where the manager struggles with how to keep team members motivated in the face of limited career opportunities? So, I asked Amy what advice she has for managers who need to have difficult conversations with their team members about their advancement (or lack thereof) when it’s unclear if and when a promotion will ever happen. Amy shared some pragmatic pointers:

A lot of managers try to avoid these sorts of conversations because they're uncomfortable telling their direct reports that they're not able to give them what they want but, unfortunately, that's part of your job as a manager. Sometimes you have to deliver bad - or ambiguous - news. For managers like Sam's there are three things I'd suggest doing when you need to tell someone they won't or might not get a promotion.

• First, explain the process for making the decision. There's a concept called "process fairness" in which you keep people informed about why decisions are made. The idea is that if the understand why a decision was made (or hasn't been made yet), they're more likely to accept the outcome even if it's not the outcome they want. If Sam knows how decisions are made about promotions, what criteria are used, etc. he'll be more open to whatever news you have to deliver. (Joel Brockner does a great job explaining this concept in his HBR article “Why It’s So Hard To Be Fair”)?
• Second, emphasize what value the person brings. Most of us want to be seen by our managers and leaders so articulate specifically what value you see the person delivering to the organization. Mention specific projects, tasks, or responsibilities and make a direct connection to how they help the company. ?
• And third, when you have to tell someone, they're not getting something they wanted, make clear what they are getting. So, if you can't offer a promotion, can you offer a learning opportunity or explain what exactly the person can do to set themselves up for a next promotion.

Throughout this conversation, make clear that you are a partner to them in the process of their career development and don't try to sugar coat things. They will see right through that.

?So, the bottom line is this – when it comes to managing your career, having the conversation (regardless of how uncomfortable they might be) is critical. Otherwise, you are trying to navigate with no direction. And even if the feedback you get is not the one you wanted, at least you know what you’re dealing with, and you can move forward accordingly. And if you’re the boss, do your part – provide the information your team member needs to so that they can make the career decisions that are right for them.

Have you struggled getting clear feedback from a manager? Have you felt challenged providing career feedback to a team member? How did you approach it? Share your experience in the comments.?

Thank you for reading my LinkedIn newsletter! And thank you so much to Amy Gallo for her sage advice. Amy is a contributing editor at Harvard Business Review , co-host of the Women at Work podcast, and author of the newly released book Getting Along: How to Work with Anyone (Even Difficult People), which was named a book of the month by the Financial Times . She is also a speaker, coach, and writer.

Don’t forget to subscribe, and please join me and many others in the?Coaching Real Leaders Community, where I host members-only live Q&A’s, CRL episode debriefs, and more.

Catch Sam’s episode, “How Do I Get Promoted Without ?A Clear Path?" and all Coaching Real Leaders episodes on?Harvard Business Review,?Apple?or wherever you get your podcasts.?