Delivering hard truths to great people

© Pete Longworth

© Pete Longworth

Last week while I was visiting Student Maid HQ, I had a tough conversation with one of the best people my company has ever hired. His name is Greg, and he’s given me permission to share this story in hopes that it will help you.

Before I tell you about our discussion, here’s some important context: Greg epitomizes Student Maid’s values. He is one of our most requested team members by clients, his coworkers love working with him, and he’s the first to volunteer to help with new company initiatives. He’s always at the office at least an hour before his shift; he takes it upon himself to hand out business cards and drum up sales for Student Maid everywhere he goes; and he frequently invites his teammates to join him at community events so they can spend more time together outside work. He’s compassionate, kind, and a fantastic representation of our culture. Any organization would be incredibly lucky to have him…

...which is why our conversation was so difficult. Greg asked to meet with me because he wanted me to know he planned to apply for a role at Student Maid that will soon open up. And while that may seem like great news, here’s the thing: I knew he wouldn’t get the job—for the third year running. 

For the past two years, Greg has applied for this position, which we open up once a year. Each time, we’ve turned him down. Just like we did with the other candidates we didn’t choose, we talked with Greg after each interview about areas in which he can grow to improve his chances of being chosen next time around. Greg took our feedback to heart, and while he certainly has grown in some areas, the truth is that he does not naturally possess the strengths candidates must have in order to hold this particular position: He’s not detail-oriented, and he isn’t skilled in task management. When he works on projects, he misses important steps, and that often means someone else has to get involved and help him. We count on the people in this role to manage the details themselves, and from experience, that’s just not Greg’s wheelhouse.  

When Greg asked to meet with me, I knew that we would still not select him for the role. I had two choices: Let him continue to think that he had a chance, or be real with him. I chose the second.

I believe it’s a leader’s job to deliver hard truths to our people, even when it sucks. It’s hard to be honest with someone who is putting in the work and wants it more than anything. But it’s our responsibility to understand people’s unique strengths and put them in situations in which they will thrive. When they want something they aren’t suited for, we have to tell them, no matter how hard it is. We can’t lead them on only to crush them in the end. Or, even worse, give them the position out of guilt and let them fail, which hurts both them and the organization. I’ve made these mistakes too many times as I’ve built my company. I knew I had to tell Greg the truth.

When we met, I told Greg that despite his best efforts, he’s still not great with the details, and I gave him specific, recent examples of times he’s failed to follow through. For those reasons, I said, we wouldn’t be able to give him what he wanted. But then I asked him to consider whether he would really be happy in a position that requires him to spend most of his time in areas where he is weak. That sounds exhausting, frustrating, and unfulfilling. It sounds a lot like pretending to be someone you’re not.

What I told Greg is what I tell many people: You have to own who you are and who you aren’t. No one is great at everything. Over the years, I’ve had to learn and accept my own shortcomings. I’m not a great executor; I too get bogged down in the details; and I have trouble prioritizing. If I continued to pretend to have strengths I don’t have, I would only hurt myself and the company. Someone who has them as their natural strengths will always be better than me. On the other hand, put me in a room of people and ask me to paint a vision, inspire buy-in, or get a team excited about possibilities any day. That’s where I thrive. It all really boils down to this: We are at our best for ourselves and our organizations when we are authentically us.

It was hard to say all of this to Greg, but in the end, he was thankful. We want people to be real with us. We want the hard truths. But I didn’t feel right leaving the conversation there. I believe that when you know someone is dedicated to the company and is the best example of your culture and values, you have to give them opportunities to thrive and realize their potential. I told Greg that instead of applying for the position, he should create one of his own. One where he can let his relationship strengths shine. I empowered him to suggest a way that he could contribute to Student Maid on a larger level, and maybe we could build a new role for him around that. I’m excited to see what Greg comes up with.

Last week was hard, but it was important. It’s a reminder of the realness that’s required with leadership and the importance of delivering hard truths even when it hurts. We have a tremendous responsibility and opportunity as leaders to guide people toward a path of success and fulfillment. Doing otherwise not only hurts them, but it hurts our organizations too.

Hope Greg’s story inspires you.

Big hugs,