Our backs were against the wall. It was my team of 12 sales reps and I at the company standup, and I was shaking. We’d just raised a big Series B, and everyone was expecting big results.
But the team was struggling.
We were way behind quota with just a week to go. It basically wasn’t going to happen, and my team and I felt down on our luck. Something needed to happen. My team needed a spark, and I’d been racking my brain for days to figure out what that’d be. But up to that point, I’d drawn blank...
Find yourself in a similar situation? I feel for you. Being in charge of a struggling sales team is never fun. You’ve got the weight of everyone’s expectations on your shoulders, coupled with this almost panicked urge to hop on a table and give some sort of epic ra-ra speech that motivates an amazing comeback.
But like anyone who’s been in this situation will tell you, motivating a sales team isn’t that simple. It requires leadership. It requires empathy. And it requires a lot of grit.
After being thrown into that gauntlet more times than I can count, I learned that it can be done. In fact, anyone can do it. There’s a science to it. A repeatable system. And today, I want to teach it to you.
In this post, I’m going to break down the sales leadership philosophy I’ve developed helping dozens of startup sales teams. Then I’ll give you some actionable tips you can implement right away to motivate a turnaround with your sales team.
But before I do that, let me finish my story…
How I Motivated My Team When Sales Were Down
The entire company was packed in our small conference room for an "all hands" meeting. There wasn't enough space in the room and 10 people had to stand outside and cup their hands over their ears just to hear. I was one of those people.
The CEO was giving his update and said: "As for the SDR team, they’re not going to hit quota this month. Not even close."
My jaw hit the floor. You never claim defeat before the final bell tolls.
"Hey!" I shouted a little too loud as I squeezed past my colleagues into the conference room. The entire company was staring at me and you could hear a pin drop.
"Don't count us out. Does it look like we’ll hit quota? No. Not even close. But what I can tell you is that if ANY team can do it, it’s this one. Do NOT count us out."
The next day I pulled my team aside in the morning and addressed what happened. We all agreed. We were going to make them eat their words.
What happened next was nothing short of amazing. I’d never seen my team so fired up. They were cheering each other on, laughing together, and booking more meetings than they even thought possible.
Over the next four days, they broke their "most meetings booked in a day" record twice.
And when the final bell tolled, we were short by one meeting.
You would’ve thought we’d beat our quota by 200%. They didn't care that we missed our team quota by one. They were ecstatic that when everyone in the company thought we couldn't get close, we did. And they kept it going, too. The next month was the biggest we’d ever had.
Now at this point you’re probably thinking, “Okay great Kyle. You pulled a Friday Night Lights and rallied your team. But how can I do the same for my team?” Well, there’s a reason I told that story.
The experience taught me something very important. Something that’s come to form the basis of my entire sales leadership philosophy.
If your sales team is struggling and you want to motivate a turnaround, then the most important thing to keep in mind is this...
The Emotional Wellbeing of Your Sales Team is the Key to Success.
Yeah, we talk about metrics and figures and quotas. But when it comes to sales success, there’s really one factor that dwarfs all the rest: emotion.
You see, every single buying decision is motivated by emotion and justified with logic. Yes, even in B2B.
When a prospect gets excited by the software you’re selling, it’s not really because it’s going to help their company be more efficient or profitable. They get excited because it’s going to help their career. It’s going to help them make more money or earn the recognition of their peers. Or, oftentimes, it’s going to make their lives easier by taking a frustrating process off their plates.
Those are all emotions.
So when your sales team members get them on the phone, it’s their job to find that emotion, amplify it, and direct it towards a buying decision.
And in order to do that, they need to be in the right headspace. They need to feel confident. If they don’t, they won’t be able to empathize well with the prospect. They won’t be able to hype the prospect up and amplify their emotions.
And this’ll cause them to struggle.
This is the same phenomenon you see in professional athletes.
We’ve all seen it. The death of a sibling ruins a rookie’s hot streak, or becoming a parent spurs an underperforming player to turn it around. It’s the same with sales. It doesn’t have to be something outside the office - maybe the new software sucks and the glitches are making everyone stress out.
My point: your team’s emotions affect their performance. So if you want to motivate your sales team, you need to build a culture that inspires your reps and makes them enjoy coming to work.
If morale is low and you need to increase sales, improving the culture is the first place I’d look. Next, I’ll share some tips you can implement right now to do just that.
7 Tips to Build a Winning Sales Culture
1. Build Trust by Listening To Your Sales Team
No, this doesn’t mean you need to acquiesce to every demand. It just means listen. The troops on the front line know how brutal the battle is - and you need to hear them out if you’re going to be their general.
Communication with your team is the fastest and easiest way to get to the bottom of a sales slump. When salespeople know they’re being heard, it builds trust.
So when your team is struggling, the first thing you need to do is ask for their feedback. You need to create an open dialogue, and make sure they feel heard.
So try asking them a few questions like...
- What are their biggest frustrations?
- What is the biggest barrier to hitting their quotas?
- Who (or what) do they need more help from?
- What can leadership do to support them?
- What solutions and resolutions are they expecting from leadership?
If you’re going to motivate your sales team, it’s important that they feel like they’re being heard.
For instance, I’ve seen a situation where one veteran rep got funneled all the best leads. Everyone else worked really hard, but even with twice the effort they couldn’t get the same results.
Naturally, it made the other salespeople resentful, frustrated, and unmotivated. If they’d have felt comfortable making this known to leadership, they would have done it. But at the time, they didn’t... Turnover was (predictably) high, and performance (equally predictably) low.
It’s crucial to cultivate an environment where everyone feels like their voice matters. Your team needs to see that their thoughts and concerns will not only be listened to - but actually taken into consideration.
2. Use Sales Contests to Boost Morale
You can’t have lulls on your sales floor. When there’s a lull, the energy is dead - the meetings don’t get booked and the deals don’t get closed. So when you see a slump happening, you’ll want to get that energy back up ASAP.
One of the most effective ways to do this is by encouraging a sense of friendly competition.
How do you do that?
Have the AEs, sales managers, or even one of the founders come in and do cold calls vs. each other. Let the reps bet on them. Make it a spectacle.
It’s no secret that sales professionals are competitive, so spectacles like this can be a fun way to shake things up when the mood is getting stale.
I did this once during my startup days.
It was one of our slowest days in an already slow month. One of our founders, a self-professed cold-call wizard, had been giving our Sales Manager a hard time for a couple weeks.
It was all in good fun, but one day, the Sales Manager wasn't having it. When our founder wandered onto the floor and made a little remark, he threw down a challenge.
“Cold call contest. Me vs. you. Right here, right now.”
And that’s what happened. Our sales leader and our founder, battling out their professional beef on the phones. Everyone on the floor was silent, watching with bated breath.
Our sales manager was the first to book a meeting, and the room erupted in cheers. The energy was totally renewed. It’s not just about entertaining people for a moment. We were given a masterclass in cold-calling and a dose of inspiration all in one go.
3. Make Team Motivation Part of Your Daily Routine
Spectacle is useful, but big flashy moments are for short-term boosts. Pulling the “SALES ARE DOWN” alarm and deploying the motivational posters every time your team’s mood drops is tiring.
That’s because motivation is a lot of work to get going. Jump-starting a dead battery takes a lot of juice. Doing it every month is unsustainable.
Luckily, motivation also has inertia.
Once you get it going, it’s a lot easier to maintain momentum than if you’re starting and stopping all the time. That’s why I made a point to motivate my team every day.
When I ran an SDR team for a startup, I began each morning with a brief team meeting. I’d point out the previous day’s wins, and talk about what to improve upon today, and check in with my team.
I’d also set a daily objective, and rally everyone around it. But there was a catch - every SDR had to be 100% on board.
If even one SDR didn't think the objective was reasonable we’d stop and discuss. Sometimes, their concern was valid and I’d adjust the objective. Most of the time I would explain my reasoning, usually backed up by math, and end up getting the SDR on board.
This works only if you foster a culture where SDRs feel comfortable disagreeing with management. If they don't, this feedback loop won't occur and your SDR team will be average or below... Not what we are striving for.
After the daily morning team sync, it was off to the races. The SDRs would go into their days aligned around the objective we’d set and motivated to attain it.
The takeaway? Motivate your team on a daily basis.
4. Foster a Good Relationship Between SDRs & AEs
The SDR and AE teams should work together as a cohesive unit. But at a lot of organizations, this isn’t what happens. Oftentimes, there’s a lot of friction between these teams.
At many companies, you might see SDRs getting frustrated because AEs "can't close their meetings", and AEs getting frustrated because the SDRs "don’t send enough quality meetings".
Not a good team dynamic.
And yet, you see this type of misalignment all the time. And it could be seriously hurting your team morale.
When this happens, your only recourse is to bridge that gap. Close the chasm and get your teams working closer together.
For instance, when I saw that mutual frustration happening to my startup SDR team, I knew they needed help.
They were working their butts off, but for whatever reason were struggling to book meetings.
So I asked the AEs to work side-by-side with the SDRs.
“If the SDR team doesn’t move the needle better,” I told them, “nobody is making any sales this month - or next month. It’s in your best interest to offer a little help building back up your pipeline.”
The AEs were great salespeople, and they stepped up. They sat down with our SDRs and made cold-calls with them, coached them on emails, and shared helpful tips and tricks from when they were SDRs. They’d started the week grumbling about the SDRs. Now, they were high-fiving them for every meeting booked.
Their expertise elevated the SDRs, not only lifting their spirits with camaraderie and inspiration, but providing them with useful lessons and tools. They didn’t forget those lessons or how to communicate better with the AEs.
5. Use Narrative to Motivate Your Sales Team
Startups change. A lot.
This state of flux requires employees to adapt quickly and often. It can be exhausting. Building a narrative around each of these changes is how you can motivate the team and get them on board.
Narrative (i.e. a story) provides essential context and structure for understanding change, allowing our brains to process new information faster and retain it more thoroughly.
The result: employees adapt more quickly and are less burned out by frequent or major changes.
Once, the founder of my startup dropped a huge change in our laps.
We decided to change our entire target market. Yeah. Big decision.
Because of this, my team was going to have fewer leads and entirely different messaging. Needless to say, they were going to be less than thrilled. In order for us to be able to execute, I needed to get them excited about the change. I needed them bought in.
The first step: Get the leader on board. Fortunately, that was easy. I was their leader, and already fully on board with our new strategy.
The second step: Help everyone understand. The team needed to understand the reason behind the change and agree that it was necessary. Change is hard. Change that feels arbitrary is a lot harder. They needed context for the change.
The third and final step was the most challenging. The team needed a strong motivator to push them to execute. This is where narrative came in.
When it came time to tell my team about the change they jumped on board quickly. There were a few concerns that I addressed and then we shifted our focus quickly. I attribute how well received it was to the narrative I used to explain the change.
Here is the template I used to construct the message and successfully motivate the team to execute.
The "why" behind this change:
What happens when this change is successful:
What this means for them:
How we can exceed expectations:
Now I use this template every time.
You have to expect change, not just react to it. Create a plan that covers "what to do" and "how to communicate it" for major outcomes (new leadership, hirings/firings, etc).
6. Make Sure Your Goals are Attainable
Setting goals is one of the greatest responsibilities of a sales leader. A general setting a goal for their forces to accomplish must think very carefully about if it is attainable.
Attainability is also about laying out the path to victory in micro-goals. Generals don’t command their soldiers to win battles, they give specific objectives which they know will increase the odds of success.
This means breaking down your sales goals into attainable micro-goals, or KPIs.
Maybe 100 demos as a monthly sales target is overwhelming, but you know your team can convert 30% of good conversations into meetings. Your KPI micro-goal could be: “Let’s just have 10 good conversations today!”
Focus on the step in front of them - not the whole mountain!
7. Care About Their Lives Outside of Work
I believe that your quality of life impacts your quality of work. If you’re killing it outside of work, your performance is also going to rock. If you’re miserable in your home life, you’ll experience burnout and your work will suffer.
It goes back to our “professional athletes” metaphor. Feelings affect performance.
This is why I strive to help my team with their lives outside of work, and why I consider this an essential aspect of motivation. If you don’t invest in your employee’s general wellbeing and happiness, you’ll never be able to motivate them.
In addition to having more motivated and fulfilled employees, there is another benefit of helping your salespeople with their life outside of work.
They won't want to leave the company.
Companies that invest in their employees and help them grow as individuals retain those people. That's a fact. By investing in your team and helping them grow professionally and personally they will follow you loyally. Combine that with a team filled with the right people in the right role and you will have an unstoppable sales team.
Personal Goal Setting workshops were one of my favorite ways of connecting with and motivating my team. Once a quarter, we would all get together in a conference room and spend two hours going through a goal setting worksheet I developed.
Here is the high-level outline.
- Past quarter reflection
- Past quarter questionnaire
- Life assessment
- Future vision writeup
- Current quarter goals questionnaire
The workshop was to help everyone on the team achieve something they’re striving for. Just because the goal isn't work-related doesn't mean the company won't benefit from that achievement. If one of my salespeople wants to lose 30 lbs, I am going to help them create a plan and hold them accountable. I will congratulate every milestone they share with me. I do this because I truly believe that when they are 30 lbs lighter and feeling fit and healthy, their work-life WILL improve.
It’s Time to Start Motivating Your Sales Team
Alright. Sales have been down for long enough. The team’s morale needs rescuing. Let’s put an end to this.
As you’ve gathered from this post, leading a sales team is about more than just optimizing the sales process or looking at numbers in your CRM. You need to take care of your people.
Start by sitting down with your team and hearing them out - the first step toward an emotionally healthy headspace, and the foundation of high morale.
As Michael Jordan said, “The mental part is... what separates the good players from the great players.”
Now it’s time to lead your players to greatness.