3 Key Leadership Lessons for Building Highly Motivated Sales Teams

In this article I am going to take you through my three key lessons on leadership and how to build highly engaged, high-performing sales teams.

But first, I want to take you on a journey. It was the winter of 2011, and I had just left my job at CareerBuilder to take on my first job as a sales leader. I would be the director of sales at Hearst Media. I was thrilled! My team was the recruiting team, so coming from CareerBuilder, and working for a company that sold advertising and had a partnership with Monster, I knew I could be successful.

I started the way I think many new leaders do. I sized up my team and very quickly started putting practices in place. Dial metrics, email metrics, scripts, talk tracks, new offerings–I saw so many areas I could impact by bringing my knowledge as a top salesperson at CareerBuilder to this new role. 

I was convinced everyone would like me, follow me, do exactly what they were told to do. After all, it would make them successful; it was exactly what their leader did—they just needed to do it. I couldn’t wait to have a bunch of mini-me’s running around crushing their numbers.

Instead, the feedback I got was that I didn’t know their business, they were different, they had been around for years, they thought they were successful already. The system started to reject me, so I leaned in harder, got more direct. If only I could prove they were wrong and I was right, they would figure it out, fall in line, and we would be successful together.

If I had only read the book “The First 90 Days” and listened to its teachings, I could have avoided all of this. My major takeaway from that book—an eye-opening realization once I read it—was simple:

It doesn’t matter how good you are. Until you get to know your people, and they trust you and believe you understand them and the business, you will get pushback from them. 

This was my first major learning, and I’ve taken it with me to all new jobs since. Now I spend the first few months learning and building relationships before I try to make changes.

This is a must, you can’t create effective change without trust, and no one trusts a stranger until they feel they understand them and their businesses. 

This is one of the most common errors that new leaders make, which brings me to my three leadership lessons:


1. You work for your people and your team; it is not the other way around.  

This was a tough lesson for me to learn. When I thought that I could just tell everyone the “right” things to do (i.e., exactly what I would do if I was selling), and magic would happen, what I didn’t account for is this: They weren’t me, and I was not them. 

I now see that everyone is unique, but it took a long time to get there. This lesson means that it is you and your team members against their quota. It is your job to figure out how they tick, what they care about, who they are as a person, what their strengths and weaknesses are, and how you can tailor your leadership style to them. Your job is to empower them to be their best selves. When they need you, you are there. When they struggle, you lift them up. When they need support—internal or external—you give it. You work with them to help them figure out the right solution, and then help them execute it. 

Yes, this sounds like a lot of work. It would be easier to just tell people what to do. But that doesn’t work. If you want the team to be engaged, you can’t just bark orders. You need to build a relationship based on mutual trust and collaboration. Yes, there is a power differential, but it is still a relationship, not a dictatorship. Think about it like you would any other relationship. 

What would happen if you just told your significant other what to do all day, every day? How long would that person stay with you? Not very long, I suspect. The leader/employee relationship is the same. If people feel understood, if you tailor messages to them, put them first, empower them, and have their back, they can do amazing things and will walk through fire for you. Remember, as a salesperson you would do all this work to understand your client, and tailor to your client to get a deal. You were great at that right? Well, your employee is now your client. Create this dynamic and your team will lean into you and the strategies you come up with together.


2. Use a strengths-based coaching approach that leverages weekly check-ins. 

What do your 1:1s look like today? Are they asking about forecasts, staring at accountability metrics and directive on actions? As Marcus Buckingham, the father of strengths-based leadership says, “If you don’t have time to understand near-term work and how you can help, stop doing everything else, and just do that.” He is right. I learned this during my time at ADP, when we bought The Marcus Buckingham Company and quickly rolled out all his teachings. 

So, what does this look like? It’s simple. Ask your people: “What are your priorities this week, and how can I help?” Make sure they show up with around 5-10 priorities, and work to understand their plan and how you can help them execute on that plan. If they have gaps, or activities you know need to happen that aren’t listed, ask questions around those things. Follow up on what their priorities were last week and how they did. Seek to understand roadblocks that are getting in their way, and work to remove them through strategy, by fighting internal battles as their leader or by helping as a sponsor with external communications. 

If you haven’t learned yet that there are multiple ways to get to the same end result, well, I am telling you that there is. This is where strengths-based coaching comes into play. If your goal is to have your team set a certain number of meetings, open/progress opportunities, close deals and/or build internal/external relationships, strengths-based coaching means understanding that how you would accomplish those goals and how others do it, are different. 

Maybe some people can bang out 200 dials and get some meetings, but when you try to apply that to someone who hates dials, you will fail. Maybe they like email, social, or are great at networking and asking for referrals. The trick is understanding how someone works best, and then helping them maximize that. 

Now I understand there are some mandatory activities. When this is the case, try to make them fun. Otherwise, lean into your folks where you can to leverage their own unique strengths. There was a member of my team at ADP that had amazing relationships with her internal partners and could get them to bring her into every meeting they had. If I held her accountable to setting meetings the same way another member–who used social selling and email campaigns–did, she would have failed. She set more meetings then that person did, and she did it in her way. 

My favorite approach was always these methodical drop campaigns with 14 touch sequence follow ups. If I tried to have the rest of my team do that, they would likely be successful, but they wouldn’t be happy or engaged. Figure out what someone is good at, then align tasks to help them use that strength to accomplish a goal.


3. Situational Leadership allows you to be the leader your people need.

What is situational leadership? No, it isn’t “Knowing what to tell people to do in every situation” as a terrible leader once said to me. It is all about understanding the level of competence someone has at the task they are being asked to do. There are four buckets to this:

  1. Directing – For someone who has never done a task before. 
  2. Coaching – For someone who has done the task a limited amount before.
  3. Supporting – For someone who has done a task successfully multiple times, but still needs some help.
  4. Delegating – For your master; they have been there, done that.

Let’s relate this to a real-world example. Say you were being tasked with leading someone through cooking a Thanksgiving dinner. If that person has never cooked that dinner before, you will need to provide them with every recipe and all necessary gear, and tell them exactly what to do and when; it is highly directive and there is no room for any deviance. 

Now, say that person has cooked the same meal with others, or some parts by themselves. You may ask them their plan and help them tweak it, but still, you will tell them what to do and how to do it. But you heard them, and they feel heard. This is coaching. 

OK, so say you were supporting a person who has cooked multiple Thanksgiving dinners, but maybe not for you. You ask them their plan, you maybe tweak if needed, but you let them go cook. This is supporting.

Lastly, you have your classically trained chef who has cooked this dinner many times, and it always comes out good. You simply tell them, “Go cook me Thanksgiving dinner.” You get out of their way and you know it will be good in the end. This is delegating.

What do you think would happen if you were directive to your master? How would they feel? Micromanaged, right? What if you delegated to your novice? They would feel lost, right? What if you trusted the person you were coaching who showed promise, but gave them no direction? They seemed confident, but the outcome would be at risk.

This is the trick; you need to show up as the leader the person needs based on their competence on the task. Remember, this is not a global assessment, it is specific to the task, not the person. You can have all different levels of competence by task per person. Your job as the leader is to figure that out and show up as needed.

That’s it folks. Work for your people harder than they work for you, understand their priorities and how you can help, leverage their strengths, and show up as the leader they need. If you do these things your team will be engaged and will enjoy working for you, and you will get the results you are looking for.

  • Originally published November 2, 2020, updated January 7, 2021