Specialties: Strategic and Tactical growth for Membership Organizations, Business Management & Development


Does this describe you? Your business is growing and you have a great team in place—but you’re working harder than ever. You’re still struggling to free yourself from your business, despite reaching your goals.

Or how about this? You haven’t reached your goals and you’re feeling alone, discouraged. You’re starting to doubt that you’ll ever get there.

This may shock you, but I’m going to tell you that whether you see yourself in that first scenario or the second one, you have the same problem: You need a #2 who can think like #1.

What is a #2?


When I talk about a #2, I’m talking about a wingman or woman. Not an assistant, to get some of those daily tasks off your plate, but a full-fledged partner who supports you (the #1) in all aspects of your business. Think Maverick and Goose in Top Gun (without the unhappy ending, of course) or Danny and Kenickie in Grease. A #2 is an apprentice, training to be able to step into your shoes whenever they’re needed.

Let’s look back at those two scenarios: In the first one, you’re doing a great job of bringing in business and you’re delighting your customers, which brings in even more business. You’ve built a team to deal with that awesome growth, but you’re still too busy managing everything and everyone; the business doesn’t run without your constant attention. That’s because you’ve become a victim of your own success. A growing company needs more than just a growing team; it needs growing management, too. That’s where a #2 comes in. A #2 knows how all the pieces of the company work together and can keep things running smoothly; they can put out fires and even see the smoke before it becomes a flame; they give you the confidence you need to be away from the office without worrying about what’s going on while you’re gone.

What if you find yourself in that second scenario, the one in which you’re working hard and haven’t achieved your goals? This is also a situation where a strong #2 is indispensable. We’ll talk in a minute about what makes a good #2, but one obvious requirement is that they care about the success of your business and want to contribute to that success. They are the second head in the saying “two heads are better than one.” They can brainstorm and strategize new approaches with you; they make you feel less alone. Here’s another saying for you: “It’s lonely at the top.” If you have a #2, it doesn’t have to be. Plus, when you and your #2 do start achieving your goals, you’ll already be well set to start living your life because they’ll be there, ready to hold the fort.

(Whichever scenario you find yourself in, you may be so entrenched in your business that you can’t even imagine what it’s like to have a life. If that’s you, check out my blog How to Start Dreaming Again.)

How to Find Your #2

Let’s start with a truth: You don’t find a #2. You find someone who can become a #2. You spent a lot of time getting to where you are, and there is no one in the world who can do what you do—until you develop them. So what you’re looking for is potential. As you go through your monthly mentoring meetings with your team (you do have monthly mentoring meetings, right?), keep an eye out for that person who is enthusiastic about your company’s missions, who lives its values. Look for someone who offers solutions and searches for opportunities. Don’t worry so much about their current skillset: Most companies develop a siloed team naturally, so if you look for someone well-versed in every aspect of your business, you’ll be looking forever. What you want is commitment and adaptability.


Another word about potential: The person you’re looking for might not be sitting there thinking, “Man, I would make a great #2!” Many people who will make great managers and leaders don’t see themselves that way at first. They might think, “Well, I am so sales-oriented; I wouldn’t know how to mentor an employee,” or “Gosh, I don’t know anything about finances, so I could never been a good manager.” They might not think about leadership at all. Your job is to look beyond what someone is now to what they could be.

Once you think you’ve identified the right person, do them and you a favor and invite them to have a series of conversations about them becoming your righthand. This is an opportunity to confirm your hunch that they’re right for the job and for them to begin to envision themselves in that kind of position, if they don’t already. It also gives you both a chance to get to know each other better. I hope that you already have a good relationship with the members of your team (if you need some tips, check out my blog Creating an Environment for GREAT Things to Happen), but you can always learn more—and you should with a #2. You’ll be working very closely with them, and you need to build a relationship built on trust and respect.

How to Develop Your #2

Developing your #2 is a process. I’ll repeat myself here because it’s important: You spent a long time getting to where you are, and there is no one currently in the world who can do what you do. Your #2 will not learn by osmosis. They won’t even learn by you rattling off everything you know. In order to transfer the wide range of knowledge you have accrued by running this business, you need a framework. A framework gives structure to that transfer of knowledge. It ensures that you cover all the bases. It gives your maturing #2 a reference tool. Perhaps most importantly, a framework prevents you from making assumptions.


For instance, you don’t want to make assumptions about what your #2 does or doesn’t know how to do. Let me give you an example: You’ve been at this a while; you probably have a good idea how to mentor and manage employees. You might assume that someone who has been mentored and managed has picked up how to do that themselves, just by being mentored and managed. In reality, it’s hard for most people to learn indirectly like that, by being the recipient. Most people learn by doing; if they’re suddenly expected to mentor or manage someone, they’ll do their best by looking back at their own experience, but they will inevitably miss important elements. Learn more about the difference between doing a job and managing a job in my Coffee With a Coach with Performance Specialist Jennifer Perrow.

You also don’t want to make assumptions about what your #2 does or does not enjoy doing or what comes naturally to them. Maybe you absolutely love numbers. Revenue goals, closing ratios, the number of appointments you need to bring in each week—you are totally into it. You love it so much that you can’t imagine anyone not loving it. If you stop to think about it, though, you probably know plenty of people who don’t love numbers. Your #2 might be one of those people. Maybe they don’t like numbers because they don’t understand them, or maybe they just don’t like them. (That’s not a deal breaker! I’m sure there are things you do in running your company that don’t turn you on.) A framework encourages you to go step-by-step through your processes so that you uncover gaps in knowledge and learn where your #2 needs support.

What kind of framework should you use? There are a ton of them out there; if you have one you like, use it. If you don’t, I’m a fan of the 5 Functions of Business. Here’s a quick overview of the 5 Functions and some of the knowledge you might deliver in each:

  • Bringing in Business: cover the strategies you use for networking, marketing and selling, as well as how to manage and monitor those strategies.
  • Getting the Work Done: cover how to organize time and tasks with block timing, and how to develop, implement and improve processes and procedures.
  • Creating Raving Fans: cover how to deliver service that surprises to every customer, every time; include your client care process and the process you use to solicit reviews and referrals from happy customers
  • Hiring and Training: cover the culture and values of your company and how to hire and train the right people for the right positions; don’t forget to cover how to develop and mentor employees and how to delegate work
  • Administration and Finance: cover the company’s strategic plan, which should include your vision, mission and organizational structure; cover how to calculate and interpret financial numbers that indicate the health of the company; go over all the behind-the-scene tasks that have to get done

Above all, be patient. Remind yourself as frequently as you need to that you spent a lot of time getting to where you are—and have frequent check-ins to review the progress that your #2 is making so you can feel good that you are moving forward and accomplishing this vital transfer of knowledge.

How to Motivate Your #2

By now, I hope you’re comfortable with the fact that this process is going to take some time. I promise I won’t say it again, but you spent a lot of time getting to where you are; if you’re honest with yourself, it wasn’t always a smooth road. If you use a good framework, your #2 will have a shorter, smoother road. But there will be those moments of frustration and discouragement; that’s natural when you’re learning new skills. Here are three tips to keep your #2 engaged, invested and motivated:


  • Know Their Why. Just like your own Why, your #2’s Why is what keeps them going when the going gets tough. What is important to them personally? What do they want out of life? How can you help them achieve that? Share your own Why with them, too; it’s entwined with the vision the mission of the company they’re helping run.
  • Keep Them Growing. Hopefully you learned in that series of initial conversations why your #2 is interested in being your #2. That’s not the extent of their professional ambitions, though; anyone who signs on as your #2 wants to learn and grow. What other professional goals do they have? What do they want to learn? How can you help them achieve that?
  • Give Them Ownership. You asked this person to be your #2 because you think they have something to contribute. So let them contribute! Encourage them to bring their ideas to the table and implement them. Increase their ownership as they develop their skills and mature professionally.

When you invest in your #2’s professional and personal goals and interest, you show that their success matters to you. Being appreciated and valued is a great motivator.

How to Back Off So Your #2 Can Succeed

At the end of the day, this may be the hardest part: Letting your #2 actually behave like you, the #1. You’ve been doing this on your own for a long time; you have got this down. It can be difficult to watch someone not do things as well as you do—or exactly the way you do them. That’s why you need to get out of the office and give your #2 the room they need to practice and perfect their new skills so they can thrive in their new position. Here are four tips to getting yourself to back off:


  • 1. Repeat this to yourself: This person is not me. They have their own style, their own approach. They don’t have to do things my way. They just need to meet my expectations. Repeat as frequently as necessary—which may be a lot at first.
  • 2. Communicate your expectations. I have to admit something to you: When I first ran a business, I was all about everyone who worked for me looking busy. If they weren’t busy when I popped in, they weren’t working. It didn’t matter to me that they might be taking a break because they had just accomplished some awesome project; I was about appearance, not reality. Don’t be like I was! Define your #2’s success in terms of measurable results.
  • 3. Celebrate success: There will be times when you need to step in and mentor (or even correct). But look for opportunities to praise, too. Recognize and celebrate successes, even small ones, especially at first. A taste of success is a great motivator to reach for more success.
  • 4. Get out of the office. Remember that the whole point of having a #2 is to free you up from your business so you can have a life. Live that life! Schedule a class or activity that takes place during the work day. Plan a trip that starts on a Friday. Bug out early on a Wednesday to have coffee with a friend. Your maturing #2 needs room to grow, and you need to live the life you’ve always dreamed.

When you look at companies who have achieved their goals, they have one thing in common, regardless of industry or leadership style: The owners always have a #2. If you want to hit your numbers, and even surpass them, if you want to build the business you’ve always envisioned, if you want to live the life you’ve always dreamed, it’s time to get yourself a #2.

(If you want other tips on how to free yourself up even more from your business, check out my blog Letting Go to Grow.)

When you can be away from your business and have the confidence that everything is being taken care of, that’s true success. And what about when your #2 finds themselves wanting more time outside the business? Then it’s time to get them a #3!

This is a subject near and dear to my heart, so if you want to talk about how to get your own personal wingman, drop me a line.

For a deeper dive on the topic, reach out to one of our Certified Business Coaches™ for complimentary coaching session Click Here



Companies we’ve worked with
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Organizations we’ve worked with
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Franchises we’ve worked with
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Associations we’ve worked with
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