A Letter to all Enterprise Leadership Teams

I have sat down to write this letter more times than I can count. I have truly and deeply debated the angle to take. Should I be direct, abrasive, kind, dramatic, deeply empathetic. I have settled on calm and clear with a little discomfort for the both of us.

The goal of this post is to have you read this in your weekly leadership meeting. The output, for you to deeply think about your organization’s culture, alignment with one another, ability to live in reality and truth seek.

Little about me. I have worked for different sized companies: Start-up, nine-billion dollar enterprise, 90-year old mid-size, and SaaS growth tech. I have had many positions: Director of Product, Director of Marketing, Chief of Research and Development, CEO, Founder, Inventor, Emergency Medical Technician, Mentor, Sales Representative, Chief Product Officer to name a few. In many operating models: Hardware, software, hardware-software, high scale manufacturing and SaaS. We good? Cool.

Now that we know each other. Let’s get into the reason for writing. Wherever you are right now I want you to ask the people sitting around the table, what is your organization’s health? Not revenue, not operating income. How do people feel coming to work today? When people commute into your office do they get sweaty palms, nervous chills, depressed, pitt in stomach or just loath to walk through your doors? In juxtaposition explain to your team how you feel about your own drive into work. If both of those feelings are the same or out of alignment. Meaning you feel great, but you know that your teams have different feelings toward you or your organization. Then mission control we have a problem. If all is peachy, then please by all means stop reading…

See your job as a leadership team is to do nothing else but to make sure your teams, every last individual, feels valued. Don’t sit there and say to one another “that at this size and scale Nate, it’s impossible for me to actually impact daily work” or make each individual contributor feel differently. Not true. Please think very deeply about the alignment of the culture, vision and more importantly your strategic execution of this strategy at the individual contributor level. How transparent are you being with the entire corporation about why “we” exist as a company?

This has nothing to do with your management incentive program and all the objectives built around these metrics. No, this is much deeper. Why does your company exist? What’s is its purpose in the market? Does your company make the world and it’s employee’s a better place for humans? Does your team in weekly leadership meeting focus on the “F” not the “A”?Do you talk about the people and the great work they do and the hours they dedicate to make other people’s lives better? Do you get to know them outside of work? Because work you guys, is part of our daily fabric. People take their jobs home with them everyday. They have shared mental boundaries and if those boundaries are deeply intrenched around a negative and unhappy culture, vision, and strategy. This is playing out at home.

Why? because the law of primacy is in full effect. People are affected by their daily purpose and meaning in the world. Income is a factor but people want to feel like they have a deep sense of purpose in the role they play. People are very intelligent even though we may joke other wise, they can feel when they are being taken advantage of. They can feel when there is misalignment. Align them! empower them, make them feel valued. IT IS IN YOUR CONTROL. You can leave this meeting right now and take action. You can impact humans. You can change their life at home and at work. You can make yourself uncomfortable and ask them about life no matter what the SVP of HR says. It’s hard to deeply explain the amount of emotion I am feeling but I want you to imagine I am looking you in the eyes. Filled with emotion and pleading with you to re-align your organization around your sole mission and purpose of why you exist. Remember, you don’t exist to keep this enormous hierarchy stood up and channel manage. It’s to center people around your product, the people that use it and the purpose it serves.If the purpose it serves causes harm to humans or is deceptive in anyway. You CAN change the direction. When your employee’s see you take action and physically re-align the company around greatness it is inevitable employee’s will feel empowered to make a similar change. In addition, the clearer you can connect their contribution level within the company with how they can impact “their” customer . It’s over. People’s motivation, drive and love for life and work becomes deeply impacted. Because they can see one of the most valuable aspects of your business, customer elation.

Please forget about yourself and get to work. Be empathic. Help them see this. If this is sparking emotion for you and you can feel inside that change is needed then speak up and be heard. Help your team get there.

Yes, I know, re-alignment can be painful and feel like an unclimbable mountain. But it doesn’t need to be. Take small steps. Make a plan. Create a clear and concise strategy that every person can read and get involved with. Then create a weekly cadence that you share with every person within your company. Maybe it’s town hall, 1:1’s or weekly company updates. Come back to this shared understanding and don’t leave people guessing about what this means to them. Make it mean something to them. Create new shared mental boundaries. This is your job. Your job is to surprise, delight, empower and give security to your teams. Your job is NOT to command and control but to love and nurture. This is tough to do I know. But I believe in you. You can do this.

What’s going to change: For starters the six-to-twelve nearly meaningless meetings you have on your calendar right now will disappear. They will be replaced with invites of meaning and purpose to you, the people you work with and the customers you serve. The conversation will change. In fact, you will be astonished at how fast the company will move. This huge titanic, Borgian mass will begin to move like the Starship Enterprise. Give it a shot. Not a weekly shot though. Make this a key defining objective for an entire year. Get the company thinking and believing this way. The way of, centering people around your product the people that use it and the purpose it serves.

To bring it all home. If you need some help on how to implement. I would recommend a couple books to the group. These books have inspired me and our leadership team and the teams I have had the pleasure to work with.

To be clear, I have not been paid to post about these books, nor would I do so. But I have wanted to simply share resources that have deeply impacted my life and the way I think about others. This topic of writing is a passion of mine. Why? because sometime ago I had the awakening that I needed to make a similar change. I was out of alignment and I needed someone to look me in the eyes and say “Nate! Make the change”

Kindest Regards


Our culture stance at Pluralsight: We don’t just talk about our awesome “culture,” we actively work on improving it every day. We look for candidates who embody our core values — people who are truth seekers, entrepreneurs and eternal optimists. We believe in giving our employees the autonomy to thrive in their work, driving out fear, focusing on continuous improvement, and working toward a common purpose. If you excel in an environment where you can truly make a difference and enjoy working with positive, passionate people, you’ve come to the right place.