A Simple Model to Measure and Improve your Leadership Skills

This is post #2 in my 365 Writing Challenge.


If you’re a founder, leadership is probably a topic that runs through your head every single day.

The success of your company is directly related to your ability to lead. We’ve seen companies live and die by their leadership. We’ve also seen all different kinds of leaders…good, evil, outgoing, soft-spoken etc.

So it begs the question, what makes a great business leader?

There are a lot of models, books and theories around leadership. Today I’m going to refer to this recent post from Mark Suster that really inspired me, Some Thoughts on Leadership Going into 2016.

Like the title states, this isn’t a research backed leadership model, they’re just based on Mark’s opinion based on his experience. Mark is a seasoned entrepreneur who has sold two companies and is now a well respected investor who has seen a lot of CEO’s go through the trials of building a startup. So I trust his perspective when it comes to identifying leadership.

In his post, he lays out 7 elements of a great leader:

  1. Sense of Purpose
  2. Conviction
  3. Relationships
  4. Team Building
  5. Communications
  6. Empowerment
  7. Presence

In this article I will:

  1. Do a really quick review of each one with a quote from Mark’s post and my quick interpretation
  2. Share how I’m making this model actionable

Let’s start with the quick reviews…

1. Sense of Purpose

“If people don’t know the mission there is no way to achieve the objective and you end up with a team pulling in 100 different directions – even if only by small amounts.”

This is the “why” behind why you’re building your company. It’s your vision, mission and values. It’s your culture.

Your purpose is your north star that acts as a lens through which you make decisions, and the guide rails that keep your team aligned and on track.  Most experts, Mark included, would recommend you codify your sense of purpose. Write it down, make it specific, and revisit it regularly.

2. Conviction

“Great leaders have deeply held conviction in their strategy and plans. Codifying what you believe is one thing but sticking to your plans is another.”

This is your ability to stick to your sense of purpose and your plan.

If you think of any great leader, you can see their conviction very clearly. They have their set of principles and they stick to them. That’s why people respect them, even if they don’t agree with them. It’s their conviction that allows them to make hard decisions.

3. Relationships

“People will accept being overruled or will accept compromises or will live through cut-backs and downsizing or whatever else is thrown their way when they trust and respect you. And this comes from hours and hours of investing in personal relationships.”

If you’re a people pleaser like me, you want everyone to like you. That’s not what Mark’s talking about here. In order to make everyone like you, you have to make everyone happy and that isn’t always possible. Leaders are faced with incredibly difficult situations every day. What’s important is that people respect you so that when you do have to make a hard decision, they trust that you’re making the right choice even if it doesn’t positively affect them. Respect is built on trust. Trust is built by putting in the time with people and really understanding their needs.

4. Team Building

“The hardest thing as a leader of teams is to know when it is time to “hire above” your existing team and when it’s time to let your team members try to develop into the next role.”

Great leaders surround themselves with great people. They know they can’t do it all alone and they’re aware of their own weaknesses. Building the right team is critical to building a successful business.

Mark describes one of the hardest decisions when building a team is whether to hire above your existing team, or give existing members an opportunity to grow into the role.

5. Communication

Great leaders tell people what they’re doing and why. They are transparent about the goals and objectives of the organization and they’re willing to tell people how the company is doing against those goals.

Communication is at the core of any healthy relationships, business or community. “Communicate early and often” is the rule of thumb you’ll hear in the startup world. This can be a tough one for a lot of leaders because they want to take the weight of the challenges on their own shoulders. It’s hard to communicate bad news. Communication also isn’t one of those things you can do reactively. It has to be a habit, building communication systems into your business routine. People can’t help you if they don’t know what the problem is, and you’re not doing your team any favors by not telling them the good and the bad.

6. Empowerment

You may have a strong sense of purpose, a great and differentiated product or service and a great team surrounding you but if you don’t learn to empower your team you’ll never be as effective of a leader as you should be. Empowerment is exactly what leadership is: It’s about setting the direction for the team, assembling talented players and then letting them execute to their fullest abilities.

Founders are used to controlling everything. So when it comes time to build a team around you, it can be hard to give up that control. In some ways I struggle with this too. Pretty soon I’m going to have to give up owning the core offering of our business (our conference) so I’ll be put to the test again. Empowerment isn’t just about giving people ownership over a specific area of the business though. It’s also about creating an environment where people feel like they have a voice, that they play an important role in the organization and that they have a level of autonomy.

7. Presence

“…great leaders are present. They show up in the office. They respond to email. They get involved in laborious staff meetings. They get involved in hard product decisions. They give good news and bad news personally. They know when morale is down because they are living it. They lead from the front…”

This isn’t a hard one for those of us who are bootstrapped or working with extremely limited resources. But eventually, once you build a team, it may be tempting to take your hands out of the day to day operations. There are a lot of entrepreneurs who like to travel and take extended periods of time off. That’s fine if you need that to be happy (to some extent I do too) but it won’t help your leadership. A leader is putting in the time as much or more than any other member of the team.

Making the Model Actionable

I was really inspired by these 7 elements as I felt they aligned well with my own beliefs around leadership. I often think of leadership as this one singular thing, but seeing it broken down like this made it easier to wrap my head around.

If these are the 7 elements that determine the strength of a leader, I started wondering how good I was at each one. So I rated myself. For each of the 7 elements, I gave myself a rating of 1-5. Here’s what I came up with:

Sense of Purpose: 3
Conviction: 2
Relationships: 2
Team Building: 4
Communications: 3
Empowerment: 4
Presence: 4

Average: 3.1 out of 5

Not great eh? I know I’m my own harshest critic but it definitely looks like I have a lot of room for improvement. So I also wrote down what I’m currently doing well and how I could improve in each area:

1. Sense of Purpose (3):

We have a very clear vision and mission at CMX and we’re really good at sharing and applying it regularly. This has come naturally to me because it’s something that’s so deeply rooted in our culture and purpose. Where we need to improve is in the specification and application of our values. We’ve had values but they’ve felt more like vague platitudes than something we really live by. It’s up to me as a leader to get very clear about what our true values are, write them down and make them actionable. I’ve done the first two parts…making them actionable is still something we have to figure out.

2. Conviction (2):

This is one of the areas where I need the most improvement. It’s not because I have trouble committing to my beliefs or plans, it’s because I struggle with planning. You can’t commit to a plan that you don’t have. So the first step is to get a clear plan down, based on the vision I have for the company, and then work with my team and advisors to refine that plan. Once we have something specific, it becomes much easier to commit to it, and practice conviction.

3. Relationships (2):

This is the second area where I need the most improvement. If you know me, you might be surprised by this. Most would say that relationship building is one of my best skills. In many ways it is, I’m really good at putting time in with people, I’m highly empathetic and I’m good at making friends. But as Mark says, relationships isn’t just about getting people to like you, it’s about respect. It’s about making the hard decisions when you need to. My nature and need for people to like me gets in the way of this regularly. I end up becoming friends with people rather than someone they respect as a leader. This is an area I strongly need to improve.

4. Team Building (4):

Right now our team is small but strong. Everyone working on CMX, advisors, employees, volunteers and contractors, have a deep passion for our mission. They’re here for the right reasons and that’s a standard I never want to sacrifice. They’re also highly talented and ambitious. In the future, team building will be harder as we grow but right now, I couldn’t be happier with the squad we’re running with.

5. Communications (3):

Transparency is something that comes naturally to me. I enjoy sharing and being open about learnings (as you can see in my writing). Where we really need to improve is in our system for communicating regularly so that we can get things out of our heads and in a place where we can take action on it. This also ties back to the need for more specific plans. By having a specific plan we can have measures of how we’re performing against that plan and have open conversations around how to improve it.

6. Empowerment (4):

This is something that comes to me naturally as well. I enjoy seeing the people around me succeed and I want them to feel real autonomy and ownership over their work. This will be put to the test when I hand off ownership of our conference to the person we hire to run all CMX events soon.

7. Presence (4):

Again, we’re so early and such a small team that there aren’t many challenges here. We’re all executing and have our hands in a lot of projects. I’m highly present with our team. If there’s one area I want to keep in mind as we move forward is to stay present with our community as well. I don’t want to get so heads down on work that I forget to stay present with the people we’re serving.

So with this, I have a good measure of where I’m at now as a leader and the specific areas where I’d like to improve.

My plan is to go through this process every quarter to track how I’m improving as a leader, and prioritize where I need to improve in the future.

I’d love to hear if any of you give yourselves a rating and how you think about improving your leadership. Also share any other books or articles about leadership that have inspired you. Comment below.

  • http://roypovarchik.com Roy Povarchik

    This post is right on time!
    I’m sturggling with some of the parameters and didn’t know how to define (or ever thought about measuring them).

    Here’s my questions though:
    There are times when ther is so much going on at once, how do you get the time to present enough with your team?

    • http://www.whatspinksthinks.com/ David Spinks

      Thanks Roy. The fact that you’re doing the work is the presence piece. The challenge is making sure your team is aware of the work you’re doing and your presence. That’s where communication becomes really important.