Tag: leadership

The Graduate Degree in Leadership Reading List

You can read about this on my substack.

The below is my core curriculum for the aspiring leader, manager, parent, teacher, or figure of authority who wants to be better than they were yesterday. This is a non-exhaustive list of the media I recommend for anyone aspiring to be better.

Learning rounds us out and shows us what can be better. Whenever I’ve been in a tough position at work, life, and so on, I’ve escaped to audiobooks and podcasts to learn about how to make things better.

Leadership vitruvean man leonardo da vinci. Ancient texts and leadership.

The harder part, applying what you learn, comes next. It’s possible, though, and I’ve achieved all my aggressive career goals and have started a company, Kestryl Edge LLC, based on what I’ve learned and practiced from the materials below.

So! I recommend the below Books, Podcasts, and Shows to anyone wanting to elevate their career and “Sharpen the Saw.” Learning never stops!

Disagree with my curriculum? Have an addition? Great.

Let me know in the comments below. Want more? Subscribe. I do this for free.

The Books

The E-Myth Revisited by Michael E. Gerber

Essential read for anyone wanting to start a business. It is important to read to understand the modes of failure for small companies and startup ventures.

Extreme Ownership by Jocko Willink and Leif Babin

A powerful book on mindset for leadership. A perfect first stop for anyone wanting to become a leader in any capacity. A book I’ve read and re-read. (Willink and Babin 2015)

Start with Why by Simon Sinek

The title says it all, but the book is worth the read to understand the principle and its applications. As teams look at trust building, raising EQ, and building leadership chops, so much of it comes back to Why. (Sinek 2009)

Leaders Eat Last by Simon Sinek

A great read on leadership for learning how to build psychological safety and trust in the workplace. It contains strong chapters arguing for the development of empathy in the workplace. It is a perfect read for those wanting to learn about culture building.

The Power of Vulnerability by Brené Brown

Awesome listen on Audible, very entertaining, and very moving. A perfect first read for those who are emotionally illiterate. It is a great primer on shame and professional vulnerability.

How to Win Friends and Influence People by Dale Carnegie

The archetypal “How to People” book. It covers how to be liked, how to get along well with others, and how to build relationships that work.

The Stormlight Archive by Brandon Sanderson

A five-part series that has nothing and everything to do with management, leadership, and perseverance. We learn about how to be from story and characters. The characters in Stormlight Archive reinforce the leadership lessons we learn from the non-fiction books. In the workplace, be a Dalinar, a Navani, or an Adolin.

Meditations by Marcus Aurelius

A quick and thought-provoking journal of a Roman emperor that can teach us how to remain steady in chaos. This one is great for the hot tub or the camping trip where you have some quiet to reflect and let it sink in.

Never Split the Difference by Christopher Voss and Tahl Raz

Awesome book for building confidence in tense discourse. People need to negotiate all the time, and this book provides practical tools and useful tips on how to negotiate successfully. Talking to the difficult coworker? Useful book. Talking to your boss? Useful book.

7 Habits of Highly Effective People by Stephen Covey

If you have your routines down pat, you may not need this. Routines and habits are what we build on to make long-term projects possible. If you don’t have a routine and feel like you are a slave to your calendar and your obligations, then this is a great book for you.

How to Have Willpower: An Ancient Guide to Not Giving In by Plutarch and Prudentius

Sure, there are plenty of books out there about willpower and perseverance, and this one is more of a collection of essays by Plutarch and Prudentius. This is less about hacks and more about principles you want to carve into your very being. Reading this book won’t magically grant you ironclad willpower, but taking the messages to heart and practicing the principles, over time, will.

Radical Candor by Kim Scott

I would put this in the required reading for college if I could. This is one of the best management books out there right now in terms of message, tools, and guidance. If you ever touch management roles and responsibilities, read and implement the lessons in Radical Candor. You’ll learn how to be direct without burning the house to the ground. You’ll learn key systems to building trust and rapport on a team, and much more. Buy, buy, buy!

Legacy by James Kerr

My college rowing coach had us read this rugby book together, and I think it was a formative book in terms of learning the mindset of successful team building and what it means to be great. It’s an awesome book on emotional control, sustained excellence, and relentless cultural standards. If the jackasses who are in the news are the problem with leadership and management today, then this is the cure.

The Art of War by Sun Tzu

A book that is more philosophy than warmaking how-to. The messages are clear, timeless, useful, and adaptable to most endeavors in life. This gets put on a lot of “Bro’s” must-reads for “Utter Dominance in the Manly Workplace,” which is why it can get a mixed wrap in the leadership space. My position is that if anything is controversial, you should read it and form your own opinion. You’re a leader, think for yourself. Do I think you need to approach your HR conversation with a war plan based around speed and deception? Haha, no, I don’t. Check it out; this book is a classic.

48 Laws of Power by Robert Greene

The unfortunate reality of the workplace is that your coworkers and bosses aren’t going to be Brené Brown, Jocko Willink, Simon Sinek, and Kim Scott. They’re going to be Ted from accounting and Cindy from projects. Politics, power, and manipulation are everywhere in the workplace.

My approach to this class is the same as Professor Lupin and Mad-Eye Moody as Defense Against the Dark Arts teachers. Better to know what you’re up against than to be caught Winnie the Pooh style and succumb to some numb nuts who wants to be important for the day and get in your team’s way. I’m a proponent of collaboration and the How to Win Friends and Influence People methods of getting shit done. Unfortunately, workplace bullies exist everywhere. So check out 48 Laws of Power as a research into how power works and stay allegorically strapped.

To Kill a Mockingbird by Harper Lee

Integrity matters, and doing the right thing can demand a price. Empathy is strength and prejudice is corrosive. This is one I come back to every so often.

Man’s Search for Meaning by Viktor Frankl

A transformative read on meaning, suffering, and survival. Knowing your “Why” allows you to survive the most difficult “Hows.”

If you know Why, you can bear almost any How.

Outliers by Malcolm Gladwell

I think this is in the high school reading curriculum now, which is great. A solid read on how timing, culture, opportunity, practice, and hidden advantages play a huge role in one’s success. This is where the 10,000-hour rule comes from.

The Prince by Niccolò Machiavelli

Another book on power I would say is contrarian to my noble list of wholesome recommendations. Again, know evil and know good. This is a widely read book and elucidates much on power. It’s in my Defense Against the Dark Arts curriculum with 48 Laws of Power and The Dictator’s Handbook.

Crime and Punishment by Fyodor Dostoevsky

It discusses morality, leadership theory, pride, redemption, and isolation. It is important to understand where we came from to get where we are now. It discusses the “Extraordinary Man” theory of leadership, which, until the 20th century, is the leading leadership theory we have.

Steve Jobs by Walter Isaacson

Apple is a company worth studying to know mindset, creativity, and impact. Almost all the leadership and management lessons we need to learn to be successful are echoed and alluded to in this book. Steve Jobs is a leader worth studying, and the Isaacson biography is a masterpiece.

Crucial Conversations by Joseph Grenny

Have trouble with hard conversations at work? I found your next read! This is the survival guide for the sticky talks. If you’re not comfortable with conflict and emotion, Crucial Conversations is a great read. I would say I am conflict positive, and this book is an awesome field guide reminder for how best to approach the tough stuff.

The Dictator’s Handbook by Bruce Bueno de Mesquita and Alastair Smith

Core curriculum for my Defense Against the Dark Arts class. Want to understand politics and modern power control? Here you go! The new Netflix series How to Become a Tyrant is partly based on this book.

General Recommendations

What Color Is Your Parachute? by Richard N. Bolles

If you are looking for a job or suspect you will be soon, this is THE job search book. I have nothing but positive thoughts and recommendations for this book for the professionally lost and the job seekers out there.

Norwegian Wood by Lars Mytting

A few years back, I got a wood stove and started to cut and stack my own wood in preparation for the winter. It has changed my mindset around my home, my chores, and energy systems in general. I believe this book is a great book for those chasing self-mastery and self-development. Wood is all about preparation, perfection in the repetition of tasks, learning about trees, and a fuel source that has been powering humanity for almost all of our existence.

The Brothers Karamazov by Fyodor Dostoevsky

Leadership is about setting an example. The Brothers Karamazov is a life-changing piece on what it means to be a human.

Podcasts

Huberman Lab

New to science and scientific literature? This is an extremely digestible way to get involved in science. Managers and leaders need to be making fact-based decisions. This is a great way to get exposed to science in a fun way. There are great episodes on hydration, depression, addiction, and so on; they all teach us about being human.

Dare to Lead by Brené Brown

My favorite episode is one she did years ago with Simon Sinek. They talk about the “long game” mindset and how it changes our decisions and mindset at work.

This American Life

Growing up, this podcast taught me about what it means to be an American and about life. Learn about other people and build empathy. If you feel your horizons are shallow, haha, this is an awesome podcast for you to listen to.

The Moth

Another empathy builder with stories about the human experience. There’s something healing and educational about listening to the stories of other people. Check this one out as the perfect commute companion.

The MartyrMade Podcast: “Fear and Loathing in New Jerusalem” and “The Complete Jeffrey Epstein”

History classes did us all dirty by not teaching us about the history of the Middle East. If you don’t know the major beats of the Israel-Palestine conflict, you need to spend the time learning. The Jeffrey Epstein podcast episode by MartyrMade is the core curriculum in my Defense Against the Dark Arts class. Does it make me lose my appetite? Yes. Is it important to know? Also yes. We need to shine a light on the dark areas of society in order to clean out the cobwebs.

Arnold’s Pump Club

Short, under five minutes, regular, and positive. Arnold is a huge role model of mine in what it means to be a man. Especially as he has aged, check this out for some positivity.

Shows

Ted Lasso

None of us will ever be Ted, but if we take elements from his example in the show and implement them at work, we can get the same positive effects in our teams. Ted Lasso is an awesome example of what it means to be a people-first leader.

One Piece

Yep, I have a 1300+ episode anime on my required reading list. The lessons in leadership are clear in One Piece. It is the most-watched TV show of this century, and I’d wager it will be the next. It’s a strong political commentary on global politics. The Straw Hat Jolly Roger is being used all over the world in rallies and protests against corruption and injustice. Find a way to engage in One Piece if you want to laugh, cry, and learn what it means to stand up for what’s right.

The most important step is the next one.

Dan

Be a part of the solution at www.Kestryledge.com

References

  • Sinek, Simon. Start with Why: How Great Leaders Inspire Everyone to Take Action. New York: Portfolio, 2009.

Willink, Jocko, and Leif Babin. Extreme Ownership: How U.S. Navy SEALs Lead and Win. New York: St. Martin’s Press, 2015.

Performance – Set The Team Up For Success

I’ve seen there are two kinds of managers: those who phone in performance and those who put the effort in to make it worth something for their employees. There are also those managers who think they are good at performance because they check the box, not knowing there is a heaping pile of value left on the table. They fall into category one.

I’m going to outline the bare bones of what I expect from myself for a performance cycle, and you can see how you measure up or what you’d change in my methods. This is a great article for anyone who wants to compare the performance appraisals they receive to what I would consider adequate. This is also a useful tool for anyone who is leading a team. Leaders, managers, bosses, mentors—whatever you think of yourself as—my articles are for you.

A broad outline of what “good looks like” for performance:

  • Coaching mindset.
  • Honest and direct reviews.
  • Regular time intervals.
  • Direction in line with skills and dreams.
  • Objective, provable, yes/no.

Let’s break these down.

Coaching Mindset

As a manager, your goal is to—say it with me, folks—“not be needed.” By coaching our team to improve, we give them more responsibility, make them more capable, and ideally create a high-performing team where we aren’t needed as much as we were. Extrapolating this to the context of performance, your goal is to evaluate everyone against what you measure they are capable of and find ways to help them grow and improve.

Managing doesn’t capture the philosophical attitude of growth mindset we need to have with the people in our charge. This is why I prescribe the coaching mindset. Coaches are there for the players. They build the rosters, evaluate strengths and weaknesses, and train their team for long-term performance. They understand that the strengths of one player may cover the weaknesses of another. In this way, they evaluate the whole and the player and help all people shine.

Honest and Direct Reviews

This is easy to talk about and very hard to do. There aren’t many people who can execute a direct performance review while maintaining rapport and trust with a team. Honest and direct feedback is how we grow, and people need to hear it. > If you know your team and you’re a good coach, you fully understand the work that needs to get done and the people you have to do it. In that comes understanding how all your players are doing. Who is doing extremely well, so well they could be overburdened and at risk for burnout? Who is underperforming and slacking a bit? Who is wicked smart but needs to up their delivery?

My advice for giving honest and direct feedback? Look at the good first. Be scrupulous in defining people’s strengths and the positive light they share with the work. Then, before providing feedback, ensure your feedback is measurable, objective, and in line with the person’s career trajectory.

Regular Time Intervals

Do good coaches only meet with their athletes once a year after the big game? The best time for performance is all the time. > Kim Scott writes about this in Radical Candor, a must-read for anyone who considers themselves a leader in any capacity. (Scott 2017) Waiting until the end of the year blindsides employees with your honest thoughts. It adds unnecessary tension and anxiety to the “ceremony” of performance.

In my own company, Kestryl Edge LLC, we do annual performance in the summer. No holidays and no end-of-year accounting to distract from what matters. We give feedback immediately and give recognition of work constantly. I do monthly 1:1s with my employees and treat each like a mini-performance session.

Direction in Line with Skills and Dreams

It sounds corny; it’s not. Do you know what each of your team members’ dream jobs are? If not, this is your homework assignment. Feedback is way easier to take and implement if there’s a “why” behind it.

We don’t coach for a day; we coach for a life. Imagine having a boss who cared about where you wanted to be in a few years and took active steps to help you get there. This could be you! Now go finish your homework!

Objective, Provable, Yes/No

Goals need to be provable. I train my teams to write them in such a way that no one could take an opinion on if it was finished or not. Make it black and white; collect receipts.

I’ve worked in fields where I would complete my employees’ performance appraisal and then my boss, and my boss’s boss, would change my employees’ ratings. This is, first of all, atrocious, and it makes my blood boil. Second off, there isn’t much you can do without receipts. Receipts protect your employees’ work when they do well.

Having provable goals mitigates friction from the start. It sets the expectation that the employee is personally responsible for completing their goal and for collecting the evidence of completion. The evidence is everything.

Remember, we’re coaching for the long game.

More soon,

Dan

Be a part of the solution: www.kestryledge.com

References

  • Scott, Kim. Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity. New York: St. Martin’s Press, 2017.

Don’t Think For Your Team – Training Critical Thinking

What does it look like to have a team with a lower critical thinking baseline?

  • You as a manager, team lead, or leader are making all the decisions.
  • During a crisis, you find yourself at the epicenter with no actions taken until you prescribe them.
  • The team does not act to solve problems, big or small, proactively.
  • The team waits for you to tell them what they need in order to get something done.
  • You give someone a clear goal with a well-defined end state, and you need to hand-hold through the process.
  • You are getting questions on everything that your team should be able to answer.

The problem with these symptoms is they signal your team needs some development. This list is non-exhaustive; it’s just a small list of things I’ve seen through the years. My assumption in this blog is that you have given your team the autonomy, resources, and technical training needed to achieve their job, and you understand why team autonomy and distributed power are important. If this is news to you, I’ll link some writing on this topic below in the future. In the meantime, I would recommend Extreme Ownership by Jocko Willink and Leif Babin (Willink and Babin, 2015). There aren’t other books I’m aware of that really portray why distributed decision-making is so important as well as Extreme Ownership. It’s a must-read on “Dan’s List” of books for leadership.

Critical thinking is necessary for distributed initiative and power because your team must be able to take the vision you’ve outlined, look at the problems in front of them, and bridge the gap from start to end. High critical thinking, paired with your support as a leader toward their autonomy, is a recipe for a high-performing team.

Remember, your goal as a leader is to not be needed.

How do we train critical thinking on a team?

I recently got a puppy—a fluffy, energetic “land shark” named Barnabas. Barnabas likes socks, sprinting in the backyard, and licking the ears of his patient older sister, Sage, a 7-year-old pit-mix. I’ve been reading books on dog training, and I want to share some theory and how it applies to how we train critical thinking. The fundamentals of behavioral conditioning apply across almost all animals.

One of Barnabas’s habits is sprinting to the back door and barking. He wants to go outside. If I go let him out when he approaches the back door with high energy, what does Barnabas learn? He learns that if he goes to the back door like a maniac on a mission, he gets to go outside. To retrain Barnabas, I only touch the door if he’s in a sit. If he stands up before I say “okay,” I shut the door and we start over.

It’s taken a few weeks, and I’m not a perfect dog trainer, but Barnabas is still a puppy. With that, he now sits at the door when he wants (or needs) to go outside. It’s a marked change in the energy of the house.

What changed? I stopped letting him get what he wants the way he’s used to, making it clear it’s his responsibility to control his state if he wants to go outside. I reward the good behavior and ignore the undesired actions. Guess what? This wisdom applies to all relationships, not just with man’s best friend.

Stop answering questions you want your team to know the answers to

When your team brings you a question you think they should be able to answer, don’t answer it. It’s really that simple. No need to be a jerk, either. Give guidance. Instead of answering, try some of these thought-provokers:

“How could you find the answer?”

“Who on another team could teach you how to figure this out?”

“What would your first Google search be to try and research this?”

You need to be kind and encouraging when you do this. If you regularly get mistaken for sarcastic or intense, make sure you validate the act of asking:

“Hey, nice job trying to figure this out. If I were gone today, how do you think you could figure that out?”

“That’s a good question, and I don’t know the answer either. I think you should be able to find an answer, and you can probably get it before I can. Do you have any ideas on where to start the hunt?”

Follow up with support:

“Hey, did you ever find the answer to your question?”

“I thought your plan was pretty good; did you get what you needed?”

Be their helper, not their answer; be the belay rope, not the ice pick.

“How can I help you figure this out?”

“They didn’t respond to your email asking for help? CC me and I’ll follow up with them.”

Let them come up with the plan

The team has a problem, a situation, or a project, and someone asks, “What should we do?” This is a golden opportunity as a manager to instill a culture of trust, to empower your team to take charge, and to help them grow as leaders. Seize this opportunity by not giving an answer, but by guiding their thinking process.

Use any of these:

“Okay, I understand the situation. What do you think we should do?”

“I think you’re the expert on XYZ; what would be your recommended plan?”

“This is a tricky situation because of [insert stakeholder difficulty]. How would you solve the problem, and what do you want to say to the stakeholder?”

Your job is to understand what’s going on and set the stage, then leave the plan up to your team. If the plan or direction they have isn’t great but it would work, let them go forward. My rule is to only intervene for safety concerns or for plans that might negatively impact their careers. Otherwise, them learning the lesson by touching the proverbial stove is exceptionally more valuable than telling them, “Hey, the stove is hot, don’t touch it.”

Your team is likely better at what they are doing than you are. Let them do things the way they think they need to be done. If you get in their way, they will resent you and leave you. Don’t be that boss. Trust them. If their plan lacks elements that need to be there for success, prompt them to consider the bigger picture:

“Your plan is solid. One thing I noticed is Becky from accounting usually needs X to do Y. Is there a way you could consider this in your plan?”

“This is a solid plan; I support it. Before you start, can you fill me in on how you’ll manage the safety risks of using X in the Y room?”

Model your thinking for the tougher problems

When things get stickier, more complicated, and begin to involve more teams or external stakeholders, I still maintain this is a great opportunity to let your team shine. However, they may need more of your support to be set up for success. Walk through a problem with your team to explain how you would think about it, find the gaps in their knowledge, and support them in learning what you know.

“Great plan so far. Here are some elements I might consider. Let’s go through them together.”

You’re still their support team as they lead the solution. Walking the line between back-seat driving and empowering them to make a working decision is a fine line, and one that shifts with the person and the situation. Don’t be afraid to invest the time and patience needed to coach your team to be able to tackle these harder problems.

Shifting culture from ‘problem escalation’ to ‘solution escalation’

This is something I’m working on trying to perfect, and I believe it takes time and a team that’s ready for it. We’ve all heard the advice, “Don’t take problems to your boss, take solutions.” This advice isn’t bad, but it also depends a lot on the situation you’re in and the boss you have.

As a leader, you have a lot more influence over people bringing you solutions than they do. It is very easy as a leader to resent your team for not bringing you solutions, but it is very difficult to diagnose that you are creating a culture where bringing solutions is not rewarded.

You can encourage critical thinking and problem-solving by exercising supportive and positive reactions when people bring you solutions and display critical thinking. If you follow the steps of modeling and guiding, and your team starts to exercise independent judgment, then all you need to do is blow on the embers. If they bring you a problem, slow things down, listen with empathy, and help them work through a solution.

Be the safety net

Don’t give your team a problem to solve and then disappear. If something goes wrong, take ownership of the problem like a good leader and prove to your team that it is safe to fail. Failure safety is the last piece of the puzzle, and it makes all the points before this work (Edmondson, 1999). The team needs to feel like they can fail and that they will be able to learn and come back better next time. Encourage responsible risk-taking and allow room for diagnosis and reflection when things go south.

Let them in on your philosophy

Relying solely on mirroring questions to deflect responsibility is a quick way to build team frustration. I was on the phone with my mom describing this process and she said, “Do they just want to hit ya? Haha!” The easiest way to get people on board with this style of leadership is to explain exactly why you are doing it.

“Team, this is a good problem to ponder together. Nice work bringing it to me. For context, I think my job as a leader is to not be needed. So I want to talk about the problem in a way where you can try and solve it and I’ll be here by your side if you need anything. Deal?”

Let them into your thinking. Use your communication tools to explain where your head is at and give people a heads-up on what’s coming. Maybe even give public kudos to anyone who’s solved some problems recently. The moral here is that when you talk to your team, you shouldn’t be a mysterious, shrouded mystic; you’re here to support them. Ask them if they are on board with your plan!

Hopefully, they are on board.

Cheers,

Dan

References

Edmondson, Amy. “Psychological Safety and Learning Behavior in Work Teams.” Administrative Science Quarterly 44, no. 2 (1999): 350-83.

Willink, Jocko, and Leif Babin. Extreme Ownership: How U.S. Navy SEALs Lead and Win. New York: St. Martin’s Press, 2015.

Failing Up – Promoted to Incompetence

I recently finished a classic in management satire: The Peter Principle by Laurence J. Peter. Having worked in several sizes of organizations, and with the book being somewhat dated (first published in 1969), I was pleasantly surprised by how well it holds up. It’s delightful.

The premise of the book is something all of us in the workforce can relate to: the concept that people are “promoted to their level of incompetence.” Someone does well in their role, so they get a promotion. They do well again and get promoted. All of a sudden, they are in a role they can’t perform well. Instead of rising to the occasion, they turn their gaze downward to the roles they knew well and begin to micromanage and scrutinize the poor souls who fill their past positions.

It is hilarious and maddeningly relatable. I would recommend the read.

If you’re a manager with people on your team who have been promoted to a level of incompetence, what do you do to repair the situation? It’s time for Dan’s “Three Ds” of performance improvement: Describe, Document, and Diligence.

Describe

Describe the goals and expectations. Your team can’t read your mind, so put it in writing. Make a guide. Make it explicit. Show and tell what “good” looks like. Make the goal so obvious that your team can self-measure how they fare against the expectation. This is where we always start: describing expectations.

One thing I always check for with a new team is a clear “roles and responsibilities” document that outlines everyone’s roles and what they are accountable for. I’ve had success leading working meetings to create “roles and responsibility contracts” within a team. Doing this as a group allows folks to recognize what others are responsible for. This sounds obvious, but you would be shocked at how many people stay within their own personal bubbles and have no clue what their teammates are up to.

It happens, and the solution is simple: transparency and clear, public descriptions. That’s right—save your final document in a place where everyone has access. Post it on the wall if you have to. Just make sure everyone agrees to it and has a copy. This is easier said than done, but it is critical for group cohesion.

Also, for the low performer, this provides a very clear signal regarding expectations. Giving them the benefit of the doubt, they may not know what their expectations are. Now that you’ve carefully outlined them, they may eagerly rise to the bar—and maybe even exceed it!

Document

Document as much as you can. Email is a legal document. Your company IM is likely a legal document, too. Your texts, notebooks, and lab books can all be considered legal documents.

How you use these tools depends on your situation. My recommendation is to have regular meetings with your questionable performer and document every outcome, even when the meetings are mundane. Save all these emails in a folder. People who genuinely need help will appreciate you sending notes on what was discussed. Clear action plans and to-do lists will allow them to execute, get their jobs done, and start performing at expectation.

However, people who are taking advantage of the job or are misguided in their self-evaluation (thinking they are hot shit when they ain’t) will probably get defensive. These situations can put you into hot water quickly. Defensive people who know how to use the “system” are great at making anyone but themselves seem like the problem. If you are a middle manager with a top-level management team that tends to be reactive or optics-focused, you’re going to need a paper trail. You’re going to need receipts.

So, make them.

  • Host a check-up meeting? Send out an email summary after.
  • Provide feedback on a work sample? Send an email summary with that feedback.
  • Have a weird conversation in the hallway? You guessed it! Send a follow-up email summarizing what was said.

This sounds like a lot, and it is. You will have great employees who want to become better and will need this level of attention and coaching in order to thrive. You will also have people who want to “ride the system” and need this level of accountability to improve. Finally, you will have employees who would be better served somewhere else; your documentation will be needed to justify to management that you have done your best to help, but they still aren’t a good fit.

Documentation can come off the wrong way to employees, so be kind. Keep a neutral tone. Consistency is the important part. I try to give all my employees notes after all 1:1s; then, the next time we meet, I pull up the notes from last time and go over them. This helps with psychological safety. I won’t ask about a task I didn’t assign, and their assigned tasks are in writing. That’s our contract.

Diligence

A system is only as good as the people who maintain it. Ain’t nothing to it but to do it. You must have diligence and consistency in your efforts to describe and document. The more consistently you document and the clearer you are with expectations, the easier it is to encourage high performance.

CrossFit teaches coaches to be relentless when it comes to technique. The concept is that you won’t let anything substandard fly. As a coach, we are taught to spot flaws—big and small—and work all athletes toward perfection. The same must be done in business.

We are all capable of greatness. If you continue to show up for your team, describe the goal state, and support them, they will improve. Take this coaching principle to work with you: be relentless (in a kind and thoughtful way). Your culture is only as good as the worst behaviors and habits you allow.

Stay diligent. Trust the processes.

— Dan

You can read more of my blogs here or on my substack.

You can learn more about the work I do at http://www.kestryledge.com

Three Thoughts on Bolstering Transparent Communication

Recently during a workshop, we had a conversation about how to keep the team informed with minimal time and energy investment. The discussion evolved into a broader dialogue about transparency and management communication tactics. I gave an answer in the workshop which was a shorter version of what I’m going to write here. I think the topic is something that we can always work on, and where a few simple tools and methods can make all the difference.

The ideal state of leadership communication is that everyone on the team knows:

  • Where the team is headed long term.
  • What the priorities are to get there and how their role fits in.
  • What decisions management is making, why, and how it fits into the long-term direction.

There are a near-infinite amount of ways to make this happen: hosting high-quality meetings, scheduling regular 1:1s with your team members, or having a goal board and updating it. Even the most perfect systems may not get you and your team all the way to the ideal state because of external factors beyond the leader’s and team’s control. Since we’re all busy and short on time, what are some things we can do in little time that have a big impact on team awareness and perceptions of communication? Read on, fellow traveler!

Transparency Mindset

The larger your team and company, the harder this is to implement—and the more important it becomes. Size equals communication dilution. You want your team to be able to explain to someone else at the company what’s going on and why.

“Why would you want this, Daniel?”

Great question. For starters, because then your team members are ambassadors of your vision. If they know what’s going on and why, they can help disseminate that information to less informed teammates. You have fewer people in your office asking the same thing; your team is empowered to fill the gaps.

Simon Sinek has some excellent books on this topic. If you are the kind of person who tells people “Because I said so” or “This is a management decision” (which is the same thing, just in different, bureaucratic, not-fun wrapping paper), I would highly recommend Start With Why (Sinek, 2009). It goes into some awesome examples of how empowering people with the reasons behind direction and vision helps promote engagement.

So, Transparency Mindset: if your team wants to know more, that’s a good thing and it’s a solvable issue. Your goal as a leader is to get them closer to the ideal state. No need to become frustrated or tired when people want to know more; this is a sign of engagement and caring. If people don’t know what’s going on and they don’t ask or try to find out, that is a red flag. It means you’re dealing with disconnectedness and cynicism in the workplace. I’ll have some writing out about that in the future and will link it here. For now, the mindset is that this is a good problem to work on and that increasing transparency will help you in the long run.

The Weekly Thoughts Email

You can have your meetings, your 1:1s, and your stand-ups, but one tool I’ve been using for years to great success is the weekly thoughts email. This is simple, and anyone leading a project, a team, or a group of people on a mission can use it. Every week, at the beginning of the week, send your whole team an email with some thoughts about what’s going on for you as a leader. I usually include:

  • The priority for the week.
  • Some kudos and positive acknowledgments.
  • Thoughts on some decisions I’m making and WHY I’m making the calls I’m making.
  • Important admin reminders if I have them.
  • Attached important emails or resources so the team doesn’t need to hunt for them.
  • A tidbit about my personal life.

I keep it raw. It’s an unfiltered, minimally edited, human email—almost like a journal entry or a letter to a friend. I think maybe 20–30% of my team read them each week, but I always “reply all” to my last “thoughts” email from the previous week so all the emails are right there in the chain. This email gives everyone on my team some insight into me as a leader, and I think it’s been huge in establishing that I’m a person, too. It also puts some important things into writing if you need to create a track record. It gives my team a central place to go for information. My team works hard! I don’t want them digging through emails.

Distributing Knowledge Ownership

We have many goals as a leader. One that I firmly believe in is to “make ourselves not needed.” I firmly believe that good leaders aren’t needed because they have empowered their team to do their jobs fully and autonomously without them. This means they’re experts, highly trained, passionate, and able to solve sticky problems with minimal support.

They know the end goal and, therefore, can work within the system to see the mission executed without you being there to explain priorities or help them problem-solve. This frees you, the leader, up for higher-order thinking and problems. If your team can handle the day-to-day, you suddenly get to think about how to make next year better. What broken systems need fixing that you can now engage in?

If you’re new to this space, check out the article “How I Learned to Let My Workers Lead” (Stayer, 1990). If your team is coming to you for knowledge, you have an opportunity to empower a leader on your team to fill your shoes. If you have a team lead or experienced person on the team, perhaps you can have them explain what’s going on at the next stand-up meeting. This isn’t going to work for everything, but where it does, it’s an awesome opportunity to let your team step up and own something while taking something off your plate.

Through this process, you get a reality check, less work for you, and an opportunity for someone on your team to step up. Feeding three birds with one scone. If this solution is off-putting, then you may need to invest in your team more and consider why you wouldn’t trust them with your responsibilities. Not all teams are ready for this. Neither are all leaders. And that’s okay! As Muriah, my co-founder, would say:

“You can’t compare your chapter 1 to someone else’s chapter 20.”

I have a goal to post regular blogs on these and other related topics. If there is something you want to read about, don’t hesitate to reach out! Until next time,

Cheers, Dan

References

Sinek, Simon. Start with Why: How Great Leaders Inspire Everyone to Take Action. New York: Portfolio, 2009.

Stayer, Ralph. “How I Learned to Let My Workers Lead.” Harvard Business Review 68, no. 6 (1990): 66–83.