The conversation your best person isn't having with you
Apr 28, 2026 6:16 am
Workplace Multiplier by Tola Akinsulire
April 28, 2026
Welcome to the Workplace Multiplier newsletter. Published Monday to Friday, equipping you to achieve your professional goals faster and without burnout or overwhelm.
The conversation your best person isn't having with you
Howdy ,
Most leaders believe they have an open door.
Their team has already decided it's closed.
Not because you are unapproachable. Not because you are a bad leader.
But because somewhere along the way, your team quietly concluded that your investment in the work is greater than your investment in them.
And when people believe that, they stop bringing you the real conversation.
They bring you updates. They bring you results. They bring you polished versions of the truth.
The raw stuff…the frustration, the ambition, the quiet dissatisfaction…they take somewhere else.
Or they take it to a recruiter.
I learned this the hard way.
Not from a book. From a conversation I almost never got to have.
During an appraisal discussion a while back, a member of my team told me something that took courage to say.
He told me he felt he was not getting a varied experience on the job.
And as a result, he was considering options outside the company.
Let me be honest with you about what that moment felt like.
It was not comfortable. Nobody enjoys hearing that someone they've invested in is already looking elsewhere. But I like to create that security for them to know they can raise it with me.
I knew immediately…it took something for him to say that to me.
It is not easy for staff to tell you they are exploring other options. Most don't. Most just leave.
He told me because somewhere, despite everything, he believed I might actually do something with it.
So I asked him more questions. I made sure I understood what he actually wanted…not what I assumed he wanted. Then I asked for a week to see if I could create what he was looking for.
We implemented something. We checked back. We kept the conversation open.
I did not lose him.
Now I want to ask you something uncomfortable.
Who on your team is having that conversation with someone else right now…because they have already decided not to have it with you?
Not because you are a bad leader.
But because the door you believe is open…they experience as closed.
Sit with that this week.
Tomorrow, I want to share what it actually takes to change that dynamic…and what it cost me before I got it right.
Keep winning at work and in life.
Tola Akinsulire
Your Strategic Workplace Mentor