Promoted Newsletter #2: The Best Conversation Starter so Your Boss Will Help You Develop

Uncategorized Aug 06, 2023

If you’ve followed me for some time now, you know I didn’t get the first two leadership jobs I applied for. 

It was pretty clear cut. I just wasn’t ready.

The positive side of that was, I was now on the leadership team’s radar. Even though I wasn’t ready for those two positions, they liked me, felt I had leadership potential, and were supportive of me working toward that as my next career step.

The downside was, there were steps I could have taken earlier to move my career along faster.

The biggest mistake I made: prior to me putting my name in the hat for those two jobs, my boss never knew I wanted to pursue the leadership route.

At the time, my boss, Mark, was newer in his leadership journey. Mark had done a fantastic job of building our team, bringing on great salespeople, and supporting us to be the #1 team in the company.

We were doing extremely well. We did so well that he got a country manager promotion in just a few years.

In his defense, it happened so fast none of us on the team were ready to take his position. So the company brought in someone from the outside, Greg.

He had a lot of leadership experience, and it was noticeable immediately. That’s when things really changed for me.

As part of Greg’s efforts to connect with each of us, he wanted to specifically know what our career goals were, what plans were in place to achieve them, and what actions were currently being taken.

Once Greg joined our company, my career development plan started moving, and I’m grateful that things fell into place that way. It was what I needed at that point in my career.

However, had I learned how to engage Mark in that conversation, it wouldn’t have taken me as long to start on the leadership journey, especially in the training aspect of it.

Here are a few things I could have done in conversing with my first manager that could have opened the dialogue, and my development plan, much sooner.

Expressed my Long Term Career Goals

In most cases, I feel that most people don’t know how to open this conversation with their boss due to these main concerns:

  •  Their boss won’t feel they’re committed to the current role 
  •  Boss will feel they’re trying to take his or her job 
  •  Afraid their boss won’t agree and will sabotage their efforts  

I’ve discussed this with a lot of people over the years, and while there may be other reasons, it generally boils down to these three things. These are all understandable concerns, and it’s okay to have these.

Let me expand on the mindset and approach for each.

Your boss will know you’re committed to your current role if you’re meeting or exceeding your quota. If you’re always on time, prepared, and engaged, he or she will see that.

Always be supportive of your other team members, help them out if they ask for advice or appear to be stuck. Participate on team calls or meetings. Be willing to share ideas where appropriate, without going overboard.

Ask good questions or questions that dig a thread or two deeper. It will show you’re truly engaged, and those questions facilitate discussion, thought, and progress toward solutions.

I used to worry my boss would think I was trying to take his job. Then I remembered the famous quote from Zig Ziglar: “You can have everything in life you want, if you will help enough other people get what they want.”

Get to know your boss. Ask how he or she is doing, personally and professionally. Build a relationship with them.

As your relationship grows, ask how you can help them achieve the objectives they’re being held to. Ask how you can help them lead, support, and grow the team.

Get to know what their career roadmap and goals look like. How can you help them look good to those they need to influence?

If you make it clear you’re aligned with your boss, that you want to support them and the team in their objectives, and you listen to and implement the feedback and coaching they give you, you’ll never have a boss try to sabotage you.

When you show people kindness and support them, regardless of what their position, title, or responsibility is, more likely than not, they will support you. They’ll like you, and they’ll want to see you and your family do well.

Make sure you don’t stop with your boss either.

Once you have him or her on your side, start networking with those around and above you in the organization. Make sure you state your career intent with them as well, and make sure they get to know you… directly from you.

Don’t leave this in your boss’ hands. He or she will be a big advocate for you, but you also want senior leaders to form their own opinion of you, based on their interactions with you.

This will allow them to understand who you are, how they can support you, and possibly how they can help you faster. In most cases, they have more influence and access to greater resources than your boss does.

So the next time you’re talking to your boss, whether it’s a one-on-one call, a field visit, or a regularly-scheduled performance review, open up the conversation about your career aspirations.

It simple.

Just say something like: “Hey boss, I’m really happy with how things are going and want to continue doing well in this role, and I’ve also been thinking a lot about my future and long term career goals. Would it be okay if we took a few minutes to discuss those goals and how we can work them into my development plan? I’d really appreciate your guidance and support with that.”

It really is that simple. Don’t be afraid to state your intent.

Start the conversation. It will open the dialogue, and most importantly, it will open up several more opportunities for you in the future. 



Whenever you're ready, here are 3 ways I can help you:

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  1. Buy my books:

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  1. One-on-One Personalized Coaching with me:

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