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ISSUE №159 · TEAM LEADERSHIP | CLIENT LEADERSHIP

Why Follow When You Can Lead?

At the end of September my wife and I will mark 25 years of marriage. Despite her best efforts, I fuck up with a surprising degree of regularity. I am ADHD-riddled, engaged in almost constant side quests and will let nothing get in the way of a good joke. Why she tolerates me is a mystery that will never be solved.

I may have mentioned that we have five kids (now all in their late teens and twenties), all of whom are neurodivergent in some way. When you add my chaos to the chaotic gaggle that we were lucky enough to parent, it is no surprise that my wife is a master of executive function planning. (In fact she's so good at being the executive function engine for other people that she became an executive function coach and she works with children and adults FYI - I know there's at least a couple of you in this audience that could use the guidance.)

But when I have fucked up and side-quested too hard or forgotten to do something that I've promised, my wife, almost always takes a leadership approach towards me rather than a reactive approach. Instead of pulling out the wagging, nagging finger, she asks me questions…and 83% of the time I have no idea that I am not on the straight and narrow. When she starts asking me questions, I have no idea that I'm about to learn something. 

Leadership Is Teaching, Not Lecturing

She might ask me a question like, “What else do we have to do in order to be ready for <event in the future>?” or “Hey, here are the things that I've been doing. Is there anything that I'm forgetting about?“ In her full-on, probably read every leadership book way (she hasn’t - she’s just a natural), these questions introduce the topic & spur the realization that there are almost certainly things on my side of the fence that need to be dealt with. 

I know it's not easy for her. We've talked about it and when I am being a non-cooperative man-toddler, she often would like to commit unspeakable acts of violence upon me. But she knows that top-down directions and mandates aren't effective (and in my case they are likely to generate some sort of unhelpful snark.) But enough about my shit. Let's talk about yours.

There are two kinds of leadership that we're going to talk about here:

  1. Team Leadership

  2. Client Leadership

What happens when you throw out the GTM playbook

That investor was wrong. Gamma is now worth $2B, with 50M users and more than half their growth driven by word of mouth.

They're one of 6 AI-native startups in HubSpot for Startups' free Bold Bets Playbook. Replit grew revenue 50x after half the team pushed back on the strategy. Ramp generated 100M+ views from a single stunt. Clay's co-founder wouldn't hang up a sales call until the prospect DMed him in Slack.

Each one took a GTM risk most founders would never greenlight. Each one paid off.

Team Leadership

I've talked about team leadership a lot in this newsletter and in my blog (The Next 5 Framework, The Leadership Lever, Known Unknowns & Unknown Unknowns, CEO or CE-No, The Strategic Corporal). And if you've ever worked with me, you know that I will exhort you to read the leadership chapters of Jocko Willink's Extreme Ownership. (Seriously, you should read that book)

Team leadership is the art of allowing the team to find its way forward with your guidance as a light hand. Your job is to define outcomes, roles & resources with crystal clarity and to supply endless encouragement & support. If you can’t define outcomes & provide support, even the most exquisitely crafted SOP will be useless. 

The agency leaders that have the most trouble with team performance are the ones that spoon-feed answers to the team, or demand the work, language and deliverables to be replicas of what they might deliver themselves. Team leadership is the fastest possible path to removing founder dependences. Poor team leadership makes the leader the most important part of the business. (Boo! Hiss!)

Great teams have clarity of needed outcomes, clarity around how their individual work contributes to the mission, and clarity around the resources available to them. Leadership’s job is to make it clear where that work is heading, how it creates value, and why it creates value for co-workers, the enterprise, and the client.   

When my wife asks a question like, “What else do we have to do in order to be ready for <event in the future>?” she isn't spoon-feeding me an answer, but rather giving me a trigger to help me remember my understanding of the outcome and to jumpstart my ability to assess and measure our relative preparedness. She is leading me to create my own workflow. If a workflow is something that I have created, I am much more likely to remember it, to be able to evaluate it effectively, and execute it.

How you are leading your team? Are you giving them answers or leading them to answers? Are you reinforcing their abilities to create solutions or are you diminishing their ability to create solutions by providing them with your answer? Restraint is so important in team leadership. A little struggle and a little bit of feeling stuck is often really helpful as a mechanism to jumpstart your team’s own solution strategies. When you jump in and provide an easy answer, you create the founder dependency that I know you want to leave behind. 

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Client Leadership

Client leadership is somewhat more tricky because you aren't defining the outcomes and you may not have all of the important variables  that matter to the client (strategic goals, financial constraints, etc…the list is infinite). They may not know what all the variables are, or it doesn't occur to them to share their internal goals and values, or maybe they don't think that they should. Whatever…sometimes where your client is headed is a little mysterious - to you and to them.

But because you understand how your services impact businesses and your experience tells you how the results are transformative to clients, you have to create the confidence to tell them, "This is where we se we need to go and here's why." We are using the exact same team leadership skill set of clarity and context to create a shared sense of alignment between agency and client.

Here's the real benefit of you leading your client - you set forth a path that has expected outcomes which are grounded in what is possible, reasonable, feasible, and doable.

Client leadership is shaping this as a shared discovery of the destination. You agree on how the destination is measured, eg, more leads, better profits, whatever. The important distinction vs team leadership is that agency and client have defined the outcome together, but the agency defines the path. The mechanisms you use to accomplish the goals are under your control. 

Sadly, client leadership isn’t “set it and forget”. Your client will introduce new variables and constraints, but it client leadership is the delicate art of not being reactive to the client but asking if the destination has changed. You are still fully in charge of defining the path to the destination but if the destination has changed, you have earned the right to restructure the path, and redefine what is possible. 

An agency that is reactive doesn’t take the opportunity to redefine the outcome or redefine the resources needed to reach the outcome. They simply ask “How high?” when a client change says “Jump!”.

An agency that is leading their client looks at how changes impact the destination. Do the changes mean a significant adjustment or a minor one? Has the change altered what’s possible? Does the change adjust the transformative properties of the engagement. Only after these questions are addressed will the agency decide what what actions they need to take and explain the impact to the client. This kind of leadership means translating the change-driven impacts into a language that your client understands.  

Here’s another example from my wife - when she wants me on board with something that I've already agreed to, she might say, “Hey, here are the things that I've been doing. Is there anything that I'm forgetting about? “ Via her leadership superpower, she is reiterating that there is a plan in place, and triggering me to reassess my own actions and outcomes.

When you close a client, you've already sent out the path and goals. Leadership demands you remind your clients of already defined the goals and waypoints. But changes on their side, or unexpected external influences demand that you ask questions to strategically redirect the engagement. When my wife asks about changes, she is reminding me that we have a target outcome & that I need to consider where I am relative to my contribution. By introducing the concept of change to her actions, she has opened up the possibility of a strategic redirection. When you point out changes to client variables or external factors, you, too, are inviting the client entertain your strategic redirection.

There's a lot in this newsletter and you have learned how my wife pulls me back to the straight and narrow without creating friction. She is exercising the leadership traits of clarity, a light hand, and the willingness to adjust based on circumstances but because I know there's so much here, I decided to make you a cheat sheet.

Quick Leadership Cheatsheet:

  1. Leadership isn't defining the path forward but rather making the circumstances such that your team and clients can create their own path forward.

  2. Leadership isn't about "do it this way" but rather it's about:

    1. Clarity of desired outcome

    2. The resources that need to be available and the waypoints that need to be met in order to create that outcome

    3. Communication that explains how team member contributions create value & make the path forward more clear for everyone

  3. Leadership is about sharing ownership. While you might have the big A (Accountability) from a RACI chart, your job as a leader is to make sure that the responsibility on the RACI chart is clear and resourced and has an adequate feedback loop. This is to make sure that those who are responsible for creating the results are positioned to react to goals that change and are empowered to ask for needed resources. 

  4. BONUS RESOURCE: Check out my free Let’s Fix This F*cker Before It Breaks - WTF Agency Toolkit - it talks all about pre-mortems, post-mortems, and RACI accountability charts. 

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