Be Your Sales Team’s Biggest Cheerleader


Conferences are exciting experiences.

You’re with people who share a similar mindset, dynamic speakers are teaching you neat things, and the energy is impossible to contain! You take notes feverishly on your iPad, typing as fast as the flat-screen keyboard will let you, trying to capture every bit of information you can. You leave exhausted. Exhausted, but rejuvenated.

That’s exactly how I felt after attending SalesHacker Conference in Spring of 2015. I was pumped to get home and start selling services for the company I was working for at the time, SOUTH.

Not everything at SalesHacker was applicable to my job, but many things caught my attention. One of them went something like this:

“You have to be your sales team’s biggest cheerleader.”

I had previously managed sales teams and trained sales people so the idea of cheerleading for them wasn’t foreign. I understood that the sales manager/team leader needed to bring energy. I understood that sales people got down and that someone had to keep them positive. I understood it from a management standpoint. I understood all that on paper, at least.

B2B Sales

Fast forward to 2017. Everyone told me that I should be in sales and the money seemed like a nice perk, so that’s where I’d headed a year prior. I didn’t realize how hard it actually was. Now I was struggling to cut it as a B2B (business to business) salesperson in healthcare consulting.

The amount of wins in B2B sales is significantly less than B2C (business to consumer) sales, something I hadn’t accounted for when I took the job. Especially when you’re selling complex services in a slow-moving industry like healthcare. Nor had I accounted for the fact that I don’t thrive in the face of rejection like some people. Furthermore, I had no idea I wouldn’t be getting much help.

After a year in this role I was beaten down. I didn’t have any wins to my credit, I spent most of my day in solidarity, and the role of Sales Manager had only recently been filled. He didn’t have time to babysit a flailing new guy when there was a whole position he had to carve out for himself.


I often think about my days at the furniture company. It was an important, and fun, time in my life. I think back to what I did right, what I did wrong, and why we had success throughout those years.

Back then I got good responses from the people for whom I was responsible. I don’t say this to brag. In fact, looking back, I’m not sure why they were as loyal as they were. They didn’t make great money and at the end of the day, they worked very hard with no benefits.

I treated them how I imagined I’d like to be treated and they rewarded me with trust. I taught them how to sell and, in turn, earn paychecks. I incentivized them, often with money out of my own pocket. I bought them lunch and I made sure beer was in the fridge. I helped create a fun atmosphere. When they didn’t make a sale, we talked about why and how they could do better next time.

Turns out that is how I’d like to be treated because now I’m in their shoes. And I obviously don’t have control over the environment because I’m on the team, not leading it.

Lessons Learned

These days (this was mostly written mid-2017**) I operate in a vacuum. I am a one-man show and most of my time is spent in one-way communication: sending emails and making phone calls to people who aren’t expecting me.

The line from the SalesHacker Conference has recently been my mind: “You have to be your sales team’s biggest cheerleader.” My organization isn’t setup with cheerleaders. Nobody is there to encourage them to keep going and give support. And that doesn’t make this team or the leadership bad, but the people on the team need to understand that. This team faces constant rejection, or at the very least, apathy, from the people they’re reaching out to.

One solution, the one my organization has taken, is to simply pay the sales team handsomely for what they bring in. This requires no commitment, no emotional labor. The human element of a cheerleader brings encouragement, support, and a shortened feedback loop to the sales team. There is no reason handsome wages and a support team can’t work in conjunction, though.

I don’t blame anyone in my company and I’m not bitter about this, I am simply pointing out the differences in organizational structure. Both my former company and my current one have enjoyed success with these varying tactics, and you have to figure out which works best for you. Emotional labor is difficult to scale, higher commissions aren’t.


There’s a warm and fuzzy side to this concept that can easily overshadow hard numbers. Sure, it’s fun to have a fun and positive work environment. Yes, most leaders want to give their team the best. But, when these concepts are applied, they:

  • Decrease turnover – On average, hiring a new salesperson costs $2M.
  • Increase likelihood of success – If you’re invested in your team, they will be more likely to give you their best effort every day. By using one-on-one time, you’ll get immediate feedback on how to correct course when they’re off track. This is in direct opposition to the idea of a single yearly review in which tons of time has already been wasted (imagine being told you’re doing something wrong 358 days after you’ve already been doing it).
  • Builds trust – When your team sees you working to help them succeed, they will trust you. They will embrace the processes and even things they don’t understand (i.e. new compensation packages, the distribution of leads, etc.) because they know you have their best interest at heart.

Tactical Ideas for Being A Good Cheerleader

If you are interested in being better cheerleaders, here are some ground-level ideas:

Give time – One-on-ones to create quick feedback loops. If you oversee sales people, the best way to quickly improve their performance is to review their performance with them. Listen to phone calls, critique emails, go on sales calls, and listen in on appointments. Have a powwow when it’s done and tell them what they did well and what they can improve on. Make it a safe environment to make mistakes, but let them know why you’re doing it so they can actively make adjustments without a poor attitude.

Celebrate wins – This may seem obvious, but the celebration of wins has to be genuine. Lip service, a half-hearted email, or a sarcastic announcement on a conference call will do more to discourage your people than encourage them. When someone has a win, whether that’s a new client, a first sale, or anything relevant to your business, a celebration that matches the victory should be had.

Incentivize – Bonuses, contests, spiffs, and recognition are all ways to incentivize team members. Not everyone is motivated by money, even salespeople.

Support – As a leader, positivity and energy have to come from you. Some people will naturally do that, but it’s part of your job. Be positive, no matter what. That doesn’t mean turning a blind eye to the negative, it means focusing on the positive and building on it.

Respond – One of the worst things you can do as a sales manager is blow off a team member when they’re asking for your help. Texts/calls/emails that go unanswered may seem small to the person in charge, you’re busy and there may be other things that are more important in the grand scheme. But to the person who needs help, there’s no greater indication of how unimportant they are.

Provide resources – This may mean marketing materials, it may be a book about sales, it might be access to leadership, it may even be a course you pay to send them to. Whatever it is for your business, provide it! They will appreciate the investment and they will be more equipped to succeed because of it.

Compensate fairly – Your sales persons’ goals should align perfectly (or almost perfectly) with the businesses goals. If not, you’ll be working against each other all day, every day. Align goals to get expectations and actions to follow suit.

Being your sales team’s biggest cheerleader may seem like extra work that you don’t have time for. But the positivity and encouragement that come from it will drive your team to perform better in the long run. And at the end of the day, your job is to drive sales. So what better way to do than empower the people on the front lines?

** I recently won my first (And second, it’s taken me a long time to finish this post) contract, a bid we’ve been working on for more than six months. It felt great to win and I’m ecstatic to be “pulling some weight.” The commissions will feel nice once they hit my bank account, but the most memorable part of the win was how my sales manager made a big deal of the win. He was there to cheer me on and help me celebrate our victory when the deal closed.