How To Lead Self-Directed People

Frustrated Boss and Employees
holbox / shutterstock

You worked hard to find and hire top talent. Your staff is the best of the best but for some reason they won’t do what they’re told. Sorry, but as much as you may want it, you can’t really tame unicorns. If you do, you lose the magic. The very fact that top talent is self-directed and opinionated makes them creative and driven but it also makes them hard to control. So what’s a leader to do? Don’t tame unicorns, harness the power!

I’ve been a Cloud Solutions Architect for over a decade. My job isn’t just a technical role, it’s also a leadership role – specifically, influence leadership. According to Patricia Knight, “These leaders create followers who want to follow as opposed to followers who believe they have to follow.” I lead cross-functional design and implementation teams with nothing more than the strength of my ideas and my (sometimes not-so) charming personality. I don’t have the luxury of saying “because I said so.”

Still, there are plenty of ways to fail at leadership. I have been incredibly fortunate to have had the guidance and good example of Matt Coviello, my manager of 14 years. I learned more about leadership from him than anyone. Here are some of the mistakes I’ve made and lessons I’ve learned that help me lead top talent.

1 – Teach a Man to Fish

Fly Fisherman
Cindy Creighton / shutterstock

It’s a fact that your best employees either move up or move out. They will either improve and take on bigger challenges in your organization or they will find someplace else that will help them to improve. It’s healthy and natural. You don’t need to worry about a team member outgrowing your organization. That’s a high quality problem. It’s better to have a high performer that eventually outgrows you than to have one that has “retired in place.”

I used to do too much for people when they were struggling or couldn’t do something as well as me. They say “Give a man a fish and feed him for a day. Teach a man to fish and feed him for a lifetime.” I finally figured out that you can’t really teach someone to fish when you won’t let go of the fishing pole. It can be hard to watch someone struggle. But struggling with something at the edge one’s ability is the beginning of knowledge. Mastery takes time…a lot of time. Now I put people in charge as soon as possible and then I get out of the way. The hard part is to stay out of the way. It’s OK to offer hints but I need to wait to be asked or ask if I can help.

I believe “what one person can do, another can do.” But when I help too much, I’m saying “what one person can do you can’t do.” Don’t rob your employees of self esteem and genuine learning experiences.

2 – Give Up Some Control

When the pressure is on, I start to think “If I can manage to keep an eye on everything, nothing will go wrong.” But control is just an illusion and a highly addictive one. The more control we get the more we want. Being a control addict is a surefire way to become hated. Honestly, none of us can really “watch all the things” especially on a big project. Some of us can follow more things than others, but we each have a limit to our awareness.

So, how do I ensure all the work gets done unless I’m intimately involved with all the details? The key is delegation. When I delegate, others can act with autonomy as far as the details are concerned but they also carry accountability for the business outcome. When I delegate, I’m able to work at the level of business inputs and outputs which is less to manage and also keeps me out of the way of people implementing the details.

In most cases being a good boss means hiring talented people and then getting out of their way.

Tina Fey, Bossypants

Once I delegate, I need to resist the temptation to “take over” just because the work isn’t being done exactly as I would do it. Maybe the employee has a better approach. You hired your people for a reason, right? Remind yourself that it doesn’t matter how the work gets done so long as it gets done in a way that meets business requirements. If the work doesn’t meet business requirements, it’s time for a conversation, not to immediately take away responsibility. I’ve had it happen to me and I’m sad to say I’ve done it to my co-workers. It’s pretty devastating to morale. When you do that, people get hurt and don’t trust you anymore. Work with the employee to find a resolution – ideally one where the work gets done and the employee learns something.

If you need to reassign or cancel work, make sure you have a conversation about it first. Your employee deserves to know why. Most people will assume that a reassignment is due to poor performance. If you’re just rebalancing the workload say so. If you weren’t satisfied with performance, a conversation is the start of learning.

3 – Trust Your People

It doesn’t make sense to hire smart people and tell them what to do; we hire smart people so that they can tell us what to do.

Steve Jobs

I learned pretty quickly that I wouldn’t survive as a solutions architect if I went around acting like an expert in everything and telling everyone what to do. Arrogance isn’t a winning leadership strategy with engineers or anyone else for that matter. What I learned was “You need to trust your people, not just your own understanding.” Your team has decades of combined experience that you don’t have. Don’t throw that away.

But I also learned that most of the details we argue about don’t matter that much. If it doesn’t impact the business outcome, I need to let it go. When the team can’t reach consensus, help them to see the business problem with more clarity. If the team still can’t reach consensus, make the call. But when you do, be sure to explain why you made the choice that you did and explain the factors that drove your decision. Over time your example will show your team how to make difficult decisions more effectively.

4 – Explain and Persuade

I used to get frustrated when I’d assign important work to people and it wouldn’t get done. I’d find out later that the person didn’t understand the requirements or didn’t understand why it mattered, so they just didn’t do it.

I learned that when it comes to assigning work, silence is NOT acceptance. Now I get people to verbally commit to work – by asking. People like being asked. Also, when people verbally commit, they are far less likely to withdraw from a project. People have a strong desire to be seen as consistent to themselves and others. So if the priority or importance are unclear, we get that out of the way up front.

Explain why the work matters. When people see how their work relates to the larger scheme, the quality and quantity of work increases because people understand the importance and impact of the work on others. With the appropriate context, the most mundane job can be transformed from unbearably boring into a noble pursuit.

When negotiating, all parties should feel represented. The only lasting agreement is one where all parties feel that they have had a voice. People always find a way to be heard whether through sabotage, defection, or simple non-participation. They may not get everything they want, they should get enough to stay in the agreement. Where they aren’t getting everything they want, it’s my job to make sure that they understand why.

5 – Ask Quality Questions

Questions change our focus – they change what we are thinking about, they change what we are feeling and they change the resources that are available to us.

Tony Robbins

Years ago when I was in sales, I was given the advice “Don’t ask a question unless you already know the answer.” That’s great advice for a sales pitch or a jury trial, but it’s an insane way to live. How would we ever learn anything? Questions are tools that allows us to actively shape our reality.

As leaders, we need to leverage the intellectual capital of our teams by encouraging the free exchange of ideas. When we have a problem to solve, we need to ask our team. When we do, we need to be careful about giving our own answers too quickly or too firmly. Human beings are wired to defer to authority. Once a leader makes a definitive statement that is louder or more forceful than the team, inquiry stops. When we ask questions, we need to wait for an answer – often longer than we may be comfortable waiting. Keep waiting. We have two ears and one mouth; we should use them in that proportion. If we don’t like the answers we’re getting, we need to ask a better question.

6 – Understand Motivations

Beyond money, what motivates each of your employees? Are they driven by significance, contribution, connection or something else? Our motivations define us. So you need to understand your employee’s motivations and do so without judgement. Your employee is probably not driven by the same things that you are. That’s OK. You’re both right. You have different ways of thinking so you are able to bring different ideas and strengths to the workplace. If your employees don’t know what drives them help them to figure it out. Employees that understand their motivations are happier and more productive. Once you understand what drives them, you can get more of what you need by getting them what they need.

Human Needs / Tony Robbins
Tony Robbins

7 – Make Sure Everyone Has a Role

Left Out
sirtravelalot / shutterstock

Whenever I work with someone for the first time, I ask the question “All things being equal, what would you like to work on? You may not always get to do what you love, but when people do what they love, they do a better job.” Employees often ask themselves: “What can I do for the team? How can I provide distinctive value?” By helping them to answer these questions you can more effectively connect them to your purpose and your organization’s purpose. When people don’t feel valued, that’s when they are most likely to leave.


8 – Do Your Job Not Someone Else’s

“Lead by example”, they said. “It will make you a better leader”, they said. It’s true, but I misunderstood. I used to try to coach by running around the field like a player. Leading by example is about integrity, not about actually doing someone else’s job.

You’re the coach not the athlete. When you get that confused, you’re getting in your own way and you’re getting in your team’s way. As I learned from a former manager, “Who’s doing your job while you are doing someone else’s job?” This is a valuable lesson for all employees.

9 – Manage Problems Not People

Sometimes I get upset when things don’t go my way. Like the time when I was accountable for an unexpected cloud outage the weekend of a corporate event for 10,000 partners and customers. When does blaming people ever make it any better? You pick yourself up, dust yourself off and fix the problem. That’s what my team did: we turned a job ending problem into a career defining moment instead of turning on each other.

When problems happen, put aside the emotions of the situation. Don’t take it out on your people. Don’t be insulting or sarcastic or assign grunt work because you’re upset. It’s not about you and it never was. When you take it out on your people, you miss the opportunity to deal with a situation constructively. Even if your team says nothing about your behavior, they will begin to mentally withdraw leaving you to solve problems on your own. That’s not what you want in your darkest hour.

Instead, deal with the situation in a way that brings your team together then work together to resolve it. There is only the business problem and your team’s collective ability to address it. Don’t waste energy fighting your team. Focus everyone’s energy on the business problem. When you do, you will find your team allied with you against the problem. It’s always better to negotiate from the same side of the table – respect begets respect…and loyalty.

10 – Embrace Failure

Nobody panics when things go according to plan. Even if the plan is horrifying. [When you do something unexpected]…well, then everyone loses their minds.

The Joker, Batman: The Dark Knight

Man, I hate failure. But I have to remember that failure is an essential part of life. It’s how we respond to failure that determines our destiny. In fact the secret to success is failure. We progress more quickly when we “fail fast, fail often and fail incrementally.” But failure feels terrible, so we act like it shouldn’t happen. And we don’t plan for it which makes it worse. Whenever we do anything for the first time we’re probably going to fail. As leaders we have to plan for failure by including it in our processes, our project timelines and our best practices.

Think about how many times SpaceX failed before they succeeded. They failed over and over again, but they used their failure to learn and improve.

SpaceX / YouTube

There is greatness in each of us. When we work together we can bring greatness to our teams, our organizations and our world. I’m hoping that you can use some of these techniques to make your team even better. I’m a passionate learner and I’m always looking for new approaches. So, I hope you will comment below to share your own leadership lessons.


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