Out of LineWhy Great Salespeople Fail When They Get Promoted Into Leadership
Every sales org has done this. Somebody crushes their number three years in a row. Leadership looks around for someone to run the team and says, obviously, the person who sells the most. Congratulations, here is a title, here are eight people, good luck.
Six months later the team is miserable, the new manager is miserable, and the company has lost its best seller and gained a bad manager. Two problems for the price of one promotion.
I spent 20 years in staffing, working my way up to COO, and I watched this pattern play out across the staffing industry over and over. So when Kate McKinnon came on Out of Line Episode 19, this was the first thing I wanted to talk about.
Kate saw it from the sales floor first
Before Kate built HR teams and started her own firm, she was in sales for about 10 years. Here is how she described what kept happening around her:
"You would have really talented sellers being promoted to leadership roles and failing, and also making everybody's lives miserable because they just did not know how to lead a team."
My response, word for word: "No, and nobody teaches them."
That is the whole problem in four words. Kate got so fascinated by it that she went back to school for a master's in leadership development. She asked two questions that every CEO should have to answer out loud:
- Why are companies not equipping their leaders with proper training?
- Why is leading people the only way to move up?
She put it bluntly: "You're almost setting people up for failure if the only way to move up is to lead people."
Selling and leading are not the same job
This is where most companies fool themselves. They think management is the advanced version of sales. It is not. It is a different job that happens to sit on the same floor.
| What made them a great seller | What the manager job needs |
|---|---|
| Winning on their own effort | Winning through other people |
| Taking over when a deal gets shaky | Letting someone else work the deal and learn |
| Moving fast and moving on | Explaining the why, again and again |
| Shrugging off rejection | Noticing when the team cannot shrug it off |
| Owning their own number | Owning everyone's number, and their careers |
Look at that right column. Almost none of it shows up on a commission report. You promoted someone for the left column and you are about to judge them on the right one.
The instincts that made them great can actively hurt them now. A top seller who sees a rep fumbling a call wants to grab the phone. It feels like helping. It is actually teaching the rep that the manager will bail them out, and teaching the manager that they still need to sell everything themselves. Now you have a manager carrying a full quota on top of a team, and that ends one way.
Silence turns into stories
One of my favorite parts of our conversation was about communication. Kate made a point every new manager should tape to their monitor:
"If you're not responding to your teams, people naturally, if they don't have an explanation or a reason or a story for something, they automatically come to their own conclusions and they're almost never good."
Her fix is simple: give a little context.
New managers who came up in sales are especially bad at this, and not because they are bad people. In sales, speed wins. You hear no, you move on. You do not explain yourself to the prospect who ghosted you. But a team is not a prospect. When the new manager goes quiet, changes a territory without explaining it, or skips the weekly meeting because a big deal is closing, the team fills in the blank. And they fill it in with the worst version.
"We don't have time to train"
Kate works with very competitive, fast moving companies, and she told me plenty of them claim they do not have time to train and develop their people.
Her argument is not that leadership development means piling on more work. It is that the work you are already doing gets more effective. You are going to spend the time either way. You can spend it up front teaching a new manager how to coach, or you can spend it later cleaning up a team that quit on them.
She also said something about how she measures her own work that applies to new managers: she prefers to "measure constantly" and adjust as you go, instead of waiting a year to find out if something worked. That is exactly how a promotion should be handled. Not a title on Monday and a performance review in twelve months. Check ins early, feedback from the team, and adjustments while there is still time.
What to do instead
If you run a sales team, a staffing desk or any revenue team, here is the short version.
Ask before you promote. Do they want to lead people, or do they want more money and a better title? Those are very different answers, and most people will say yes to the promotion either way because it is the only door you opened.
Build a second ladder. Give your best sellers a way to grow that does not require managing anyone. Bigger accounts, a senior title, a better split. Some of your best people should stay individual contributors forever, and they should be paid and respected like it.
Train before day one, not after the first resignation. Coaching, feedback, running a one on one, explaining decisions. None of this is natural. All of it can be taught.
Take the quota off. If the new manager still has to hit a full personal number, guess which job they will do when things get busy. It will not be the managing.
Check in early and often. Talk to the team, not just the manager. Use Kate's rule and measure as you go.
The bottom line
Your best seller is not broken when they struggle as a manager. Your process is. You took someone who was great at one thing, handed them a completely different job, and gave them nothing to learn it with.
Kate's episode goes deep on this, plus her move from sales to HR to running her own firm, the client who ghosted her and kept her work, and why she gets paid up front now. Listen to Episode 19 with Kate McKinnon.
If this is your world, you will also like my conversation with Ryan Clark on building a staffing company to $200M and Jamee Niles on why she walked away from her VP title.
Questions people ask
Why do top salespeople often struggle as sales managers?
Selling and leading are different jobs. A seller wins on their own effort; a manager wins through other people. Most companies promote the seller and teach them nothing about the new job.
Should you promote your best salesperson to manager?
Only if they want to lead people and you are willing to train them for it. If management is the only way to get a raise or a title, you are pushing people into a job they never asked for.
What training does a new sales manager need?
The basics nobody covers: how to coach instead of taking over the deal, how to give feedback, how to communicate with the team when things change, and how to measure progress as you go.
Which Out of Line episode covers this?
Episode 19 with Kate McKinnon, who spent about 10 years in sales watching great sellers get promoted and fail, then built a career in leadership development and HR.