How to Level Up Your Team and Yourself

Over the course of my career, I’ve hired about 65 people who have either reported directly to me or who have worked on the teams I’ve built. In that time, I’ve learned that industry moves fast. Even “slower” industries like healthcare are growing quickly these days – keeping up requires a constant commitment to leveling up.  

But learning and growing isn’t just important for you. Whether you lead one person or one thousand, knowing how to level up a team is a critical aspect of leadership in the modern business environment. Here’s how I do it, based on what’s worked – and what hasn’t worked – for me in the past.

Growing My Team at Single Grain

You’d think that, at a young company, hiring cheaply would have been my top priority. And on paper, it might look like it’d make the most sense to hire young workers and train them from the ground up to do the work needed at Single Grain.

But what we actually found was that, due to time and resource constraints, it made the most sense to hire manager- and director-level talent to run our SEO and PPC divisions. Even though we were limited by how much a growing agency could afford, we found that:

• Although we had access to San Francisco’s large talent pool, there was huge competition from other companies. When we found the right person, we had to act – and that often meant we didn’t have the time to test whether or not an entry-level worker could be taught the necessary digital marketing skills.
• Even if we would’ve had the time to find the right entry-level talent, we didn’t have the time to train them. We needed them to hit the ground running and be effective from day one, which often meant prioritizing experience over cost.

But even though we were hiring more experienced team members, we still had to invest in them. Things change too quickly in the digital marketing world – and in many other industries – to assume that, just because you’ve hired knowledgeable people, they’re going to stay that way. Instead, we prioritized:

• Investing in our team to help them grow to the next level
• Thinking forward about the skills they’d need not just in the next few weeks or months, but in the years ahead
• Future-proofing them for changes we thought might be coming to the industry

Recovering Stagnant Skills

While I was at Single Grain, we built it to a little under $3 million a year – largely by investing in growing our team and making sure they had the skills needed to effectively support our clients.

But it was only after I left that I realized that, despite putting so much effort into the growth and engaging with employees, I’d let my own skills suffer. When I really stopped to look at how I was performing, I found that I was actually dullest in my marketing knowledge – what I usually consider to be my core skill set.

There’s no excuse for what happened. I let my foot off the gas, and because I wasn’t continuing to learn and get ahead of the curve, I was stagnating. I had fallen behind.

Now, I devote time every week to self-improvement. That could mean working on tackling my fears or taking a skillset that’s weak for me and improving it. I suggest you make the same commitment not just to yourself, but to your team as well.

Leveling Up Yourself and Your Teams

Investing in your growth and the growth of your employees doesn’t have to be complicated. There’s a standard process you can follow – and although you may not need all of the steps I describe below, putting the relevant recommendations into practice is critical to your ability to stay current.

Step #1: Identify Your Weak Areas

At Single Grain, I didn’t see that my marketing skills were suffering – let alone what a huge problem that was. But that’s on me. Now I’m much more vigilant about monitoring for weak areas and going through the other steps I’ll describe here.

Simply put, you can’t make a plan to level up if you don’t know what you need to fix first. Marelisa Fabrega of the Daring to Live Fully website explains this in terms of gamification:

“In a game, there are very specific things that you need to do in order to level up. For example, you need to kill ten snakes and collect twenty gold coins. In much the same way, when you gamify your life you have to be very specific in terms of what you need to do in order to level up.”

Ready to find your own weak areas? The steps below may help:

• Ask others in your life where it seems like you’re struggling. This could be your colleagues, your direct reports, your clients, your family and so on. Their responses might surprise you – even if you think you’re handling everything in your life, they’ll see the blind spots you’re convincing yourself aren’t there.
• Ask yourself. Get real with yourself. Most of us know what we should be doing. But when life gets busy and work gets tough, we give ourselves permission to slack off. Make a list of everything you’ve been putting off, including all of those “someday” items that keep getting pushed to the bottom of your to-do list.
• Take a skills test or other type of assessment. Something like this may or may not exist in your industry – but if it does, take advantage of it as a useful tool for measuring your current level. Take the Google Adwords certification as an example. You might assume you could easily pass, but going through practice exams for the test could reveal some of the different ways you’ve let your skills slide.

To be clear, this process only works if you’re willing to be completely open with yourself, and put all your cards on the table. It isn’t easy to recognize that you’ve slacked off in certain areas; it was pretty embarrassing for me to realize that I’d let my marketing skills go. But if you won’t be transparent with yourself – as hard as it may be – you’ll never be able to come up with an effective plan for leveling up.

Once you’ve completed your own analysis, turn your attention to your team. What are their weak areas, both individually and as a group? Again, it’s helpful to get multiple perspectives. No manager sees everything. Let your team members rate both themselves and each other to get a fuller picture.

Step #2: Get a Mentor

Getting a mentor might seem extreme. Can’t you just take a class to help fix your weak areas?

You definitely can, but having a mentor who’s “been there, done that” helps you solve for the unknown unknowns – basically, all the problems you don’t know you need to solve yet. Even if you hire the best talent out there, there are still things they won’t know. Mentors and other experts can help solve these problems through their experience.

Mentors can also be extremely motivating, because they show you what’s 5-10 years or more ahead of you. Not only does this give you the ambition to aim for the heights they’ve reached, they can help you see how to connect the dots in new and different ways. Arranging mentorships for your teams has the added advantage of making it easier to give feedback – it’s much easier to take suggestions from someone with an outside perspective than it is from your boss.

Even better, mentors – whether you’re thinking of a single expert or a team of advisors – can be surprisingly cheap. At Web Profits, we have a sales mentor, a CRO mentor and marketing mentors so that if anyone has a question, they have a place to go. These mentors might cost us a few hundred dollars, but they’ve been much more impactful for us than attending conferences or taking online courses.

A few of my favorite places to find mentors include Clarity.fm, as well as just reaching out to the authors of books and blogs that I read. If you email these folks, they’re surprisingly likely to respond if you have a good question. I’ve even gotten emails back from Richard Branson this way (and I didn’t even have a good question for him).

Step #3: Learn from Others

Mentors aren’t just for your team, nor do they have to be people with substantially more experience than you have. If you want to level yourself up, go find someone who’s doing the things you want to do, and see if you can pick their brains.

If I’m running a SaaS company, for example, I’d want to go out and find someone who’s running a different SaaS company that’s a zero ahead of mine, or who’s successfully exited in the way I want to. Even if I can just be in the same room with them, I’ll end up getting much of the information I need – whether or not I set out specifically to learn.

You may also look at the other passive ways to learn if you are unsuccessful in finding a mentor for yourself. A good way to do this is by following what companies that are moderately smaller or larger than you are doing to get customers. Such companies do not have to necessarily be in your industry. However, these are businesses that face the same challenges as you do with respect to marketing, advertising budgets or customer acquisition. Knowing what strategies they use to gain social media followers, build links for SEO or establish authority can help you level up in terms of what works.

Step #4: Quantify Your Improvement

Professional athletes don’t just go out and practice. They plan. They take action. And then they measure the impact of that action so that they can make their future practices even more effective.

Do the same with any efforts you undertake to level up yourself or your team. Quantifying your plans will help you figure out if you’re doing the right things, or if you’re just spinning your wheels under the guise of self-improvement.

What exactly you quantify will depend on your business, your team and the skill sets you want to improve, but a few examples include:

• The number of connections you make with different experts
• The hours you or your team spend with a mentor
• Changes in your performance on the skills tests I mentioned earlier

You might have to get creative if the skill sets you’re trying to change don’t naturally lend themselves to quantification. But don’t let that stop you. No matter what or how you’re trying to level up, there’s something you can measure in order to track your progress.

Step #5: Be Patient

You aren’t going to fully level up overnight. Improvement takes time. Teams need continual investment to learn and grow, and you do too.

As a result, you’ve got to be patient and enjoy the process. As Marcella Chamorro notes in an article on Lifehack:

“Setting goals definitely helps me find direction, but sometimes I stress out way too much about the end result. By focusing on the process, I let go of the stress to achieve something and I have a lot more fun with what’s going on in the actual moment.”

Commit to ongoing self-improvement and figure out how to love the process – not just the end result. You’ll never have to worry about your skills stagnating again.

What other advice on leveling up would you add to this list? Leave me a note below with your suggestions:

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