Should You Write a Letter to Your Team?


A year ago, a CEO asked me to facilitate his strategic planning offsite for him and his direct reports. Prior to this year, the CEO had written all the strategic plans by himself because he felt that his software company of around fifty people was small enough that he was still involved in every part of the business.

For him, 2017 felt like a turning point for the company in terms of business and headcount, and he felt that the leadership team should participate in making strategic choices going forward.

We spent two days wrestling with strategic choices, weighing trade-offs, and preparing to be wrong. The team walked out of the workshop with a clear, ambitious, and inspiring strategy.

The CEO couldn’t wait to share the news with the rest of his employees.

Another year passed, and the CEO asked me to help him design and facilitate a one-and-half-day leader meeting and a two-day all-employee summit. The choices the team made in the previous year led to swift changes in how the team would approach the marketplace. The new ambition became part of the daily language and was pushing the company to test and measure new pricing, product, and promotional strategies.

The new strategy also presented a whole new set of challenges for the CEO and the leadership team. Communication of the strategy within the growing company was a struggle. The strategy was meant to be a five-year ambition, but it was interpreted that the organization must pivot immediately, and as a result, people took their focus off of the core business that keeps the lights on. Employees started to perceive the core business and, worse yet, core customers as less valuable than chasing new customers with a new product. The company continued its double-digit growth, but the pace slowed a bit. It was as if the team opened the box with a new dresser from IKEA and skipped to step 25 in putting it together. In their haste to achieve the ambition, they missed a few of the essentials along the way.

With these challenges in mind, we set to designing a leadership workshop and an all-employee summit to calibrate the growing team on the actions required for achieving the company ambition over the next year. We made no changes to the strategy from the prior year because the leadership team continued to believe it was the best path forward for the company.

One of the first moves the CEO and I decided to make was to go back to a practice he’d relied upon in years past.

He would write an open letter to everyone in the company.

The message was personal, quirky, called out people by name, celebrated wins, outlined strategic choices, and set financial targets for the upcoming year. The letter tended to be about fourteen or so pages: part review, part manifesto with editorial comments throughout. The CEO reiterated and adjusted the company mission and values based on insights gained by him and the team throughout the previous year.

Reviewing several of the previous years' letters from the CEO to employees, I was struck by how the CEO captured the perfect balance of confidence and humility. He held firm on his ambitions for the company and its place in history, but at the same time, he acknowledged his missteps and weaknesses as a leader. The level of perspective, transparency, and accountability in the letters bordered on shocking to me because I’ve rarely seen leaders so public about their personal shortcomings.

The whole experience got me thinking about how a regular letter to employees might be beneficial to a team, company or organization. Right away, the challenge I see is that it would be difficult for most leaders because it would force them to be clear about their goals, strategies, and priorities.

From my vantage point, it seems that most leaders lead one conversation at a time; reacting to the latest fires and counting on the few people who heard their words directly to relay it to the rest of the organization, like Pharaoh Rameses, in the movie "Ten Commandments," saying “So let it be written, so let it be done” and actually believing a change has taken place.

I’ve had at least ten managers in my career, and perhaps, only one of them achieved the rare level of clarity and commitment to strategy and execution that I found almost delightful in its simplicity and directness. I was a director, leading a team of six people and Conagra’s largest brand. Our previous VP had left to be an SVP in sales a year earlier, and until a replacement could be identified, I became the default leader because I was the most senior on the team. I struggled to balance the new demands and responsibilities of reporting to the business unit president directly and leading the team.

By the time the new leader had arrived, my confidence in handling the duties had improved enough to make me think I was doing the job well. The new VP wisely assessed the situation and potential power struggle ahead and decided to act before it started. He sat me down and said, “Let’s talk about roles going forward. Your new job is ‘ideas,’ and my job is ‘people and money.’” He went on to explain that my new responsibility was to develop compelling growth strategies for my lines of business and present them to him so that he could make resource investment decisions. I was no longer responsible for leading the team.

He went even further to say that I had thirty days to submit to a new strategy. I was to ignore all meetings and requests so that I could research and develop the new plan. For the next month, he rarely spoke to me other than to ask me how many days there were until our presentation. It was one of those once in a lifetime experiences where I only had one thing on my list and used the time and resources I had to focus on it.

At the end of the thirty days, my team presented a plan that approved and received millions of investment dollars, setting the brand on a positive trajectory for years to come. I share the outcome not to celebrate my strategic prowess but to demonstrate the power released when a leader can provide absolute clarity to what they want to be done. He deserves the credit for providing the clarity, space, and support needed for such an undertaking.

How helpful would it be to receive a letter from your boss or CEO every quarter?

In that letter, you would learn how the leader thinks and feels about several crucial topics such as priorities and how they link to the long-term strategy; you'd get an assessment of the competition; you'd see his or her celebrating team wins and providing recognition; you'd read an editorial on culture; and see the leader acknowledge his or her shortcomings and poorly-made decisions. Perhaps this leader welcomes your feedback, challenges, and questions that he or she would address in the next letter.

Leaders hire me to help them design and facilitate workshops for them. They think they want a strategic or business plan or to close the culture gap in their company. What they really desire is for everyone on their team to be aligned with what they are doing and how they are doing it. The depth achieved in an annual offsite led by a professional facilitator is unquestionably valuable (if I don’t say so myself) to aligning priorities, values, and strategies, but it isn’t enough. Too many things happen over 365 days for a two-day offsite to make the change more than 15-25% sticky.

What gets eroded away with time is the level of clarity and commitment to the shared vision. Without more frequent leader guidance, perspective-taking, and priority alignment led by the leader, the team will begin to make small and self-serving decisions that benefit their silo of the company. They will default to old habits and ideas that have served them well over the years regardless if it’s in the best interest of the strategy.

Hosting quarterly offsites for the leadership team would be overkill and likely a waste of resources. A better investment might be for you, the leader, to begin a practice of writing quarterly letters to employees that can serve as guideposts for dealing with the ambiguity of the future as well as keep the team tethered to the choices and agreements they made when they were at the offsite meeting and could see problems at actual size.


Where might you begin?

Step #1: Always capture notes in your journal.

Don’t just write down what happened. Write down what you’re thinking and feeling about it at the moment. Make it easy on yourself by turning to a clean page and drawing a line down the center of it. On the left side, capture what is happening, the decisions made, and who is making them. Stick to the facts. On the right side of the page, write down your thoughts and feelings about what is happening. Capture your assumptions, intuitions, and self-doubts. Having a journal full of what happened and how you felt about it at the time will help you write the quarterly letter.

Step #2: Block a day to get out of the office so that you can think.

Writing is a lost art to most of us in the management world. We make PowerPoint presentations with pictures and bullet points and send short emails and text, but we rarely sit down and write long-form anymore. Your instincts will tell you that you will need to get all your thoughts together before you begin writing. Don’t trust your instincts. Joan Didion’s “I don’t know what I think until I write it down” sums up my experience. Writing is thinking. You won’t get it right in the first draft or the second, and you can’t get to the third draft until you write the first two. Write it. Read it. Ask if it is as clear as it can be. Repeat.

Step #3: Think about your audience.

On what topics might your employees need more clarity? What can you repeat over and over again so they don’t just know it by heart but live it? What are the friction points for your people, and how might you remove them? What is changing, and how should your employees help you make the change? This letter is for your people, and they are counting on you to set the vision and help them help you get there. In a stakeholder interview with a regional president regarding one of his employees, he said to me, “He’s a president now, which means he should talk less.” I asked what percentage of the time he thought the new president talked now. He said, “50%.” What should it be? “Less than 5%.” That’s a tall order. Imagine this letter as a way of making the most of your 5% share of the talking. Give your employees the clarity they need.


Suggested letter topics:

•  Opening editorial: Summary of where we’ve been

•  Link to strategic choices

•  Business performance

•  Team culture

•  Address big questions

•  Give credit where it is due

•  Critical reflection on your performance

•  Closing editorial: project the future


I’ve written a great deal here about the benefits of writing a letter to your employees, but what might it do for you? It’s a good thing if the thought of regularly going through the practice of writing your thoughts and publishing for all to read leads to a cold-sweat and a quickening of the pulse. Think of it as your quarterly “Misogi,” which is a Japanese traditional purification practice where its practitioners sit underneath a waterfall to allow the ice-cold water “to wash away the impurity from the six elements that make up the human being, the five senses, and the mind.” The pain you might experience will induce a sense of vulnerability and humility needed to be a great leader.

You have a choice to make. Do you want to be a leader by title or by action? Be the kind of leader you wish you had. Be the leader that is confident and clear on the vision, humble enough to think he or she can’t do it alone, and human enough to admit he or she is still trying to be a better person.

Want to be more strategic?

Just imagine the impact you would have if you knew exactly how to be more strategic in everything you do and every decision you make. That is why I built See the Big Picture: Nine Steps to Being Strategic. It is a free 15-page guide loaded with simple ideas to help you transform into a strategic leader. Get your free copy here.

Jeff Shannon