The Letter I Should Have Written to My Team

The things every leaders should tell their team to set up their working relationship for success.

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A while back, I wrote a piece about the uncomfortable topics you should share with your direct reports during onboarding.

It’s unusual to dive into fears, risks, and disappointments at the outset. But those honeymoon, sunshine-filled days are exactly when you both should talk about the prospect of dark times.

Beyond the topics themselves, what I was really getting at is that while a relationship is still forming and still positive, that’s the best time to talk about the tough topics that will only get more awkward and difficult over time.

When the inevitable challenges arise, and they will, the fear that you and your direct report will be feeling will cloud your judgment. It’ll create suspicion and doubt. It will erode trust when you need it most.

What I didn’t share in that piece is how you can guide your people to more productive behaviors and how to work with you (a la your user manual).

In a world dominated by one-line tweets and abbreviated text messages, if I were leading a team today, I’d opt to write a letter to share my thoughts.

Here’s what I’d say. Please feel free to borrow.

A letter to my team

Dear team,

I’m writing to you because I want our working relationship to be as strong as possible, not just because it will help us achieve our mission and goals, but because I believe that one of the greatest gifts of work is the people you meet and the relationships you build.

Your talents and efforts will help us achieve our goals, but that’s small potatoes. I value you more than simply as a body in a seat.

What matters as much and perhaps more is how your energy, personality, and wisdom will enrich the experience of everyone on this team, including mine. You being here will make this journey more enjoyable and more memorable.

That said, I also recognize that we each have roles to fill, and that even if things are working well now, that may change in the future.

Whether it’s market dynamics, your interests, or my behaviors, the nature of work is that things change and not always positively.

Preparing for tough times can go a long way toward ensuring we do what’s best for the organization and preserve our relationship, which I hope lasts long beyond our time working together.

My mandate as a leader isn’t just to hit our short-term goals — annual targets and the like — it’s to create an organization that delivers on its promises, functions well, and has a long-term, sustainable future.

I hired you not just because you met the criteria in the job description, but because you possessed these critical attributes:

• A deep desire to grow and develop your skills and your career

• An alignment with the mission of our organization that goes beyond your functional role

• A belief that working together, we can accomplish more than if we were working apart

With all this in mind, I wanted to share with you what I wish my bosses had shared with me when we first started working together.

1. Your potential is infinite, but only if you manage it. If you see work in other areas you are interested in, ask about them. If there is a project you want to be assigned to, tell me. If you want to develop into a different role, say it. Help me help you.

2. Help me focus. My time is far more limited than my role demands. I care about you and your work, and I don’t think about either enough. I need you to make it easy for me to focus on what matters. Weekly, brief summaries of progress and obstacles, preparing for our 1:1s with a structured agenda, and creating dashboards that are easy for me to review are just some examples. Not sure, send a draft to me and let’s workshop it together.

3. Debate openly and often. Your thinking elevates the team's thinking. We will only arrive at the best answers if we can openly discuss and debate our ideas. Please know that even if I don’t agree with you, I value diverse insights, shared thoughtfully far more than I will ever value groupthink.

4. Know the why. Experimentation and exploration are valuable, but only if there is a hypothesis we are testing. If you aren’t sure about the why, ask until you get a clear answer. Always be willing to cut work that lacks a clear purpose.

5. Feedback is a gift. If something isn’t going well in our work together, tell me. Nothing will be gained by waiting. If it’s something I wasn’t aware of, give me a chance to own it. If it’s something I don’t agree with, you deserve to know. Feelings can fester, frustrate, and distract. Don’t let them.

6. When it’s time to go. Let’s talk it out and let’s plan it out. We don’t have to be dramatic, and we don’t have to have it hurt our working relationship. The best organizations have succession plans. Ideally, we’re planning together through the end and beyond.

My career was built on relationships: colleagues, bosses, clients, and partners. It is and was the way of the world. If you agree, then invite you to discuss any of the above points with me at any time.

Our journey together will not last forever. Let’s make the most of the experience and set ourselves up for far more than our shared tenure.

With respect and appreciation,