Why The "Just Delegate More" Advice Drives Most CEOs Crazy

Telling an overwhelmed CEO to ‘just delegate more’ is like telling someone with anxiety to ‘just chill out’. 

For any CEO (or leader) to be able to delegate more and so to scale themselves, some conditions need to exist:  

• A clear set of priorities that are aligned with the overall strategy 

• A strategy to begin with (which is not pretty slides with some big words and numbers on them)

• A competent exec team fit for the job at the current stage of the company (A-team rather than a team of A-players) 

• A capable set of leaders in the exec team 

• High-level of trust in these leaders (see more on this below)

• Ability to hire and fire well

• A simple, yet effective mechanism for feedback and performance management

• Self-awareness around your own zone of genius 

• Accountability culture (which is not just words buried under values on yet another set of pretty slides)

• Clear expectations on what to deliver and how to deliver (i.e. what good looks like) 

• Documented processes and how-to-guides

• And I am just getting started here… :)   

Now, let’s talk about trust. 

And more specifically, what happens when you bring on some highly experienced, accomplished execs to give you that leverage you have been starving for. The Board says: hire some big name heavy-hitters, and scale yourself. 

After the first 3 months of the honeymoon phase is when problems start. 

You have hired them for their experience and expertise in their specific area, yet, you are hesitant when it comes to giving them power.  =>  Without power and authority, they cannot be held accountable to deliver anything that actually matters for your business. => If they aren’t delivering on the most impactful goals, you (and others in the leadership team) start to wonder: “Why are they getting paid the big bucks and get all that equity for?”. 

Meanwhile, this is what they are thinking:  

“I am excited to be here and use my experience to build something big and show what I am capable of. But hang on, I am being questioned on my approach and decisions. And in fact, I don’t feel like I have the authority to make any major decisions. I thought I was brought in because of my expertise in this area, and now I am unable to leverage that. Do these people think I am making this all up / I am incompetent? Why am I here then?”. 

The 3 types of trust you need to have in any of your execs in your leadership team, in this order: 

1. You can trust that they will act with integrity, and never compromise the core values that you expect from your leaders 

2. You can trust that they will always prioritize what’s best for the business, not what serves their ego 

3. You can trust that they are competent in their field and are capable of delivering results without violating #1 and #2 

1.You can trust that they will act with integrity, and never compromise the core values that you expect from your leaders: 

Why does this matter? 

This is how they will act when you are not in the room. If you can’t trust their integrity, it’s like allowing cancer to spread in your organization. Even if the exec is a top performer, allowing them to continue with their behavior will show others what you, the leader, value by tolerating such behavior. No matter how many times you talk about the culture you want in your company, if you allow such behaviors, then that’s the culture you are going to create. 

Tip: 

When you bring a new exec on board, watch their behavior, ask their peers and direct reports what they think, and as soon as you see / hear anything concerning, don’t shy away from the conversation. For the first, maybe second time, give them the benefit of the doubt, give them feedback so they are clear on what’s expected (and watch how they respond to the feedback, it’s really telling). If their behavior continues, it’s best to remove them as soon as possible. 

2.You can trust that they will always prioritize what’s best for the business, not what serves their ego 

Why does this matter? 

Everyone has an ego just as everyone deals with some level of impostor syndrome. The question is, can they put it to the side, and commit wholeheartedly to do whatever is best for the business? Remember, your success, and the success of any leader, depends on how high-performing your leadership team is. Dysfunctional teams prioritize their own agenda (or that of their own team), rather than what’s best for the company (see more on this in Patrick Lencioni’s 5 Dysfunctions of a Team). 

Tip: 

Similar to #1, watch closely how they act in team meetings, when setting company OKRs, when celebrating wins or adressing when something goes south, etc. Are they able to “disagree and commit”? Are they blaming others for missing their own targets? 

3. You can trust that they are competent in their field and are capable of delivering results without violating #1 and #2 

Why does this matter? 

This is the hardest one to get right, and if you can’t, you are unlikely to scale your company. Or at least it will be much slower and more painful than it needs to be.  In my experience of working with scaling CEOs, this one is hard to get right because either:

=> You are not being honest with yourself about how ready you truly are to let some things go. Yes, you are ready in principle, and would love to give some of your responsibilities to someone else (and that’s what others advise you too), yet, in practice, you are holding onto some areas. Sometimes it is your intuition telling you that you should indeed be hands-on (e.g. the risk of screwing things up is too high / the consequences are too devastating). The biggest mistake you can make is to bring on an exec with false premises and expectations. It will lead to frustrations and resentment on both sides. Have an honest discussion about where you are at on your own journey and how they can best support you. You might discover that they are not the right hire for now. 

=> Even though someone has an impressive resume, you only trust their capabilities once they prove themselves. There is nothing wrong with this, but you need to be upfront with them and give them gradually harder and bigger deliverables to achieve. Use the “trust but verify” approach: give people a target to achieve, but also ask them to share their plan on how they are going to achieve it. Weekly 1:1s are often enough to have a pulse-check on progress (here is a template for that) without you being perceived as a micro-manager. If they fail to deliver results, assuming you have given them all the support they needed from you, then they should be gone within a year. Don’t let underperformers linger for too long. 

=> You want to get to the perfect outcome, your way. This has worked so far, so why change now? Well, because it’s not scalable. Either you continue with this approach, but then hire only mid-level people to execute your mandate, your way. If you hire a seasoned exec, they will rightfully expect freedom in doing things their way. Of course, they will consult you, but it is important to let them try things their way so that they can see you trust and respect their expertise (respect is especially a big one for seasoned execs). Use the “let people fail safe” approach: you let them do things their way initially where the risk / consequences are not that big and they can use the failure as a learning opportunity. Pick your battles and only take over the steering wheel when the stakes are high. How not to bruise their ego? Share your thinking and decision-making process and invite their feedback more than you think it is necessary. 

While “Trust is earned not given” holds true in some cases, in others, you need to give trust from day one and watch what people do with it. But the bottom line is, if you don’t feel like you can trust your people to 1) do the right thing 2) prioritize what’s best for the company and 3) deliver results, then you might want to change the people around you.