The Value of Coaching Your Team

"I can't help but wonder if all I needed to get rolling was for someone to show they believed in me." - Jess Brown, Lead Strategist at Content Allies.

Over the past two years, I have evolved from a solo consultant to running two companies with a total team size of over 30.

During that time, I've seen several of the team members I brought on board radically transform their lives and reach new levels of achievement in their careers that was unlike anything they were doing before.

They produce incredible work for their company and find deep satisfaction in their work at the same time.

As a result, I've come to see that my greatest value to my companies is in coaching my leadership team and leveling them up.

The value of this can't be understated, and it's something that you can start doing with your team regardless of where you are at.

In this article, I am going to share with you three stories of transformation of team members so that you can see the value of coaching your team. Then I will share tactical approaches for doing so.

The evolution of a COO

At Lead Cookie, we send over 200,000 Linkedin messages per month.
And we do it all by hand...

Needless to say, we have a lot of operational complexity at our company. Our total team size is 26 people and a majority of those are focused on the operational delivery of our service.

So how do we manage such a complex operation?

Well, I have to give massive credit to our COO, Jeff Markle, who built this operation with me from day one. Many other team members helped contribute and build this out, but Jeff was at the helm of all of this.

And now the question that is in your head...

"How do I go find myself a Jeff who can act as my COO?"

I know this is in your head because I've had countless entrepreneurs ask me this same thing.

And here is the answer...

You can't.

I didn't find Jeff who was this magical COO who was looking for a job.

Instead, this is was I found.

Jeff was working in a basic job doing events and marketing management. He was working 70+ hours per week and was working in a culture where he had to sleep with his cell phone next to his bed in fear of missing something. He was working around the clock and was totally burnt out.

To add to this, Jeff's wife was pregnant with their first son and he wanted to get out and into a career that gave him more flexibility and freedom.

So I hired Jeff. We had known each other for years, and I knew he had the right attitude and would hustle to make anything work.

But to be honest, I didn't even know he would turn out to be as capable as he is today.

Over the next few years, Jeff would work with me through multiple failed startup attempts.

And when Lead Cookie took off, Jeff was the one behind me, catching everything I threw at him and making it run.

It started with him helping me implement the work.
Then he began managing the other operational team members we brought on.
At first, it was one or two people and quickly grew to him managing a team of 10.
Soon Jeff was holding his own one-on-ones with team members.
And then Jeff was hiring team members on his own.

Today, Jeff is the glue that holds the company together. He could hop in and out of any role within the company (other than sales) and execute it flawlessly, or train someone on that role.

Jeff wasn't a COO when I hired him.
But today he manages a team of 26.

Jeff transformed himself and stepped up into this role.

Building a world-renowned Linkedin expert

Another example of coaching someone through a transformation is with Rick Williams, who is our lead account strategist at Lead Cookie.

Rick was the individual who finally let me get out of the "doing" role within Lead Cookie as he took over strategy for our accounts.

When I was training Rick, I said to him, "So do you realize that you are about to become one of the leading experts in the world on Linkedin lead generation? There will literally be hardly anyone better than you by the time you own this role."

And that is what happened.

For a while, Rick shadowed me in my role as an account strategist.
Then Rick started running his own account strategy while I shadowed him.

At first, I had to correct things or get him on track at times.

But he very quickly reached a point where I said, "Wow, you are doing better at this than I could myself."

Through one-on-one coaching, week after week, I was able to work with a stay-at-home Dad and evolve him into a leading expert in the field of Linkedin Lead Generation.

Building a lead content strategist

"I can't help but wonder if all I needed to get rolling was for someone to show they believed in me." - Jess Brown, Lead Content Strategist at Content Allies.

The quote above is from a blog post that my Lead Content Strategist at Content Allies wrote. When I read this, it almost gave me chills because I have seen an insane transformation in Jess since she started working with me.

When I first met Jess, we hired her to help fill a part-time role at Lead Cookie. At the time, she had just quit her desk job and bought a plane ticket to Asia as she was starting her journey as a digital nomad.

She was freelancing and trying to get her own business ideas off the ground while working with us part-time.

Jess was ok at the work we were doing with Lead Cookie, but to be honest, it didn't really get her excited. She was doing it to pay the bills while she was working on her personal branding side project.

Then one day, I announced to the Lead Cookie team that I was starting a new company called Content Allies.

Jess reached out to me to schedule a call. She shared how what I was building was way more in line with what she was excited and passionate about, and she wanted to do whatever she could to be involved.

I was skeptical at first, but I figured I would give her a shot.

As I started ramping up Content Allies, Jess was hustling to do whatever she could to help out. Even amidst the insane chaos as I pivoted the business model around several times, she stepped up and did her best in whatever roles and responsibilities I set out for her.

About 2 months into working on Content Allies, I saw the potential in Jess. She had an attitude and a passion that was shining through her work and I knew she was capable of way more.

So I hired her full-time for Content Allies... this was before we even had a steady business model figured out.

She stepped up and took on whatever work and responsibilities I would give her. And when we finally landed on a model that worked, she hustled to keep up with the massive volume of work in the first few months while we were getting things going.

Each week, I coached her with a one-on-one. And each week she improved, learned new things, and got better at what she did.

Today, Jess is acting as both a COO and Lead Content Strategist for Content Allies and I'm blown away by the work she is doing. My adviser, Alex McClafferty, met her and said, "Yeah, you have a rockstar on your team."

While that sounds amazing, what you have to realize is that I didn't hire some person with years of experience. This was not a clear "rockstar hire."

Instead, I hired someone who had an attitude and passion for the work, and then I've been leveling up her skillsets and mindsets to own this role.

Key Takeaway: Find someone with the right mindset and attitude. You can coach them and teach them the skills they need to excel.

Tactical Advice for Coaching Your Team

To lead others, become someone worth following

"If you want to lead others, become someone worth following." - David Sherry

This quote embodies a simple idea that is so powerful. If you want your team to follow you, and you want to coach them into greatness, then you must first start with yourself.

The reason I can coach my team is that they actually want to learn from me. They want to grow and evolve and look up to me as someone who can teach and help them grow.

Years ago, when I was struggling with weed and alcohol addictions, this would not be the case.
I would not have been someone worth looking up to at all.

But as I evolve myself as an individual, I become someone different.
I rise as an entrepreneur, and as a result, people turn to me to learn.

This may sound like a fuzzy concept, but it's absolutely key.

A wise German man once told me, "Never trust a fat businessman."

While this may sound like a harsh and prejudice statement, there is a sound reason in it.
The fat businessman is one who does not have balance in his life.
He neglects his health. And so what else does he neglect as well?

Becoming someone worth following is not just about building a better business.
It's about becoming a person of integrity in all aspects of life that people will look up to.

To coach others, you must first know yourself

Most people don't understand their strengths and weaknesses.

I know for years I didn't. Instead, you just get frustrated and down on yourself when you fail at work that is not your strong suit.

Then a few years ago, I went through a process called Unique Ability, which was focused on learning and understanding where I perform best.

The process was incredible for me and gave me an entirely new perspective on myself and how I should structure my roles to deliver maximum value.

As I saw the transformation in myself through the Unique Ability process, I began to see that each of my team members had their own unique abilities as well.

Some of them read through the book, but with others, I was able to coach and pull out of them where they were strong and weak.

We were then able to design roles for them around their strengths and offload things that were their weaknesses.

For example, Rick, who is our lead strategist, loves research, loves working with people, and making others happy. But he HATES admin work. So we did everything possible as a company to remove as much admin work from his plate so he could just focus on where he performs best.

Another example is Isaac, who is now running sales for Lead Cookie. When I brought Isaac on board, I tried to give him all sorts of different work. Some projects went great, some went horrible. Eventually, I realized that Isaac is an "Optimizer" and not a "Builder." If I try to give him a blank canvas, he will fail. But if I give him an existing process, he will level it up and take it to heights I never imagined possible.

Here's a note Isaac sent me this past week...

Screenshot 2019-07-22 14.01.34.png

These kinds of insights can only be pulled out by deep conversations with your team members...

Weekly One-on-Ones

If there is a secret to coaching your team to success, it is the weekly one-on-one.

For each of the team members I have talked about here, I have or had a standing one-on-one for an extended period of time.

Every week, we would meet. During this time, I looked for opportunities to coach, teach, or train them however I could to help them level up their game.

There is no magical structure for these one-on-ones. Instead, the serendipity of the conversation is usually what leads to the insights and revelations from the call. But I do show up with an agenda for each week that flows along the lines of the following.

  • How are you?

    • I start with this open-ended question to let them get anything off their chest. This often kicks off a discussion on the areas that they are struggling with or excelling in.

  • Discussion points

    • In this section, either myself or the individual can jot down any ideas for points to talk over during that week's call. This could be a challenge they are facing, an operational question, a teaching moment, feedback, etc.

  • The "One Thing"

    • More on this in the next section.

That is the standard agenda. Nothing crazy. I keep a Google Doc for each individual so we can collaborate in the same document each week and track notes week after week.

The key here is to invest time into the individual.

If you are doing work to evolve yourself as an individual, then you will have plenty to teach and share with others during these calls.

Who I do one-on-ones with:
I don't do one-on-ones with every team member.

Instead, I focus these with my leadership team and those who I can work with closely and make a large impact. For example, my COO is the only person on my ops team who I do one-on-ones with. I tried with others before, and it's odd, as I'm a bit too detached from their work to really make any sort of meaningful impact.

Instead, my COO holds one-on-ones with any key members of his team as he sees fitting.

The "One Thing"

As one final tactical piece to help you guide these one-on-ones, I will share a phenomenal coaching question. This comes from the book called The One Thing by Gary Keller.

"What is the one thing you can do this week, such that by doing it, everything else will be easier or unnecessary?"

This is a question that I bake into my weekly one-on-ones with my leadership team to get them to focus on a single action each week that will move them and the business forward.

Without this question, most people will flounder around and get distracted by a ton of different projects.

But this question helps them narrow in on one project they can tackle that week. Then we check in on this the following week.

This works extremely well on anyone who is in a building role at the company.

For my COO, this was crucial, as it helped him focus on the various operational systems and pieces he needed to get in place as we scaled.

For my Lead Content Strategist, this is key, as it is getting her to focus on finding bottlenecks in our processes and fixing them with new tools, systems or processes.

With that being said, this question does NOT work as well if someone is not in a building role.

For example, for Rick, who is my lead account strategist at Lead Cookie, it just doesn't make sense for him since his role involves showing up to serve our clients. There are no special projects that he needs to tackle on a week-to-week basis.

The same is true for Isaac, who runs sales. Once we realized that Isaac was an Optimizer and not a Builder, we realized that this question made less sense since he just needed to be given space to do the best he possibly could at his current role.

Invest in your team

If there is one thing I want you to walk away from this article with, it is this:

Invest in your team and they will do amazing things.

No one on my leadership team was extraordinary when I hired them. In fact, most of them were floundering and frustrated with their career path to date.

They had been in jobs they didn't like, or roles they struggled to excel in.

Through working with them and coaching them week after week, I've been able to help them all reach the potential they've always had in them.

They had the right attitude and work ethic all along.
I simply help guide them on their journey and structure their role to maximize their strengths.

This is incredibly rewarding in the results they bring to the company, but also on an emotional level. To see notes from my team and the happiness that comes from doing work that they excel at is amazing.

Invest in your people.
It is one of the best investments you can ever make.

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