Managing a sales team and coaching frontline managers - especially when they’re new to the role - requires a unique set of skills, whether pre-, mid- or post-pandemic.

How do you maintain an empathetic, human element, whilst still ensuring business results are delivered?

Attendees at our Future of Sales Festival in June 2021 had the opportunity to mine the experience of sales professionals who have faced these challenges head-on.

And sharing is caring. So here’s a selection of the best pieces of practical advice, and candid answers to our audience’s questions, from our panel session, ‘Building the Next Generation of Sales Leaders’.

Our four seasoned guest panelists discussing the subject (aaand not always agreeing) - were:

  • Jessica Nelson, Director of Business Development, Nylas
  • Catherine Freeland, Director of Commercial Accounts - Americas, Nylas
  • Jim Pattermann, Chief Sales Officer, Contelligent
  • Steve Shauck, SVP, Global Head of Virtual Sales, FIS

Here we go with the questions...

How do you manage a sales team successfully in this new ‘hybrid’ world?

How can a sales leader balance these challenges with the need to maintain confidentiality?

How do you aim to transform your sales teams to emerge into the ‘new normal’ without lowering the bar of expectation?

Psst, if you're an SEC member, you can catch the replay of this panel discussion in the OnDemand section of your dashboard.

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Q. How do you manage a sales team successfully in this new ‘hybrid’ world? What are some of the things that you’ve seen work, or that haven't worked?

Steve: We've talked about leaning into the human element, right? Do not lose sight of what your new leader - your frontline leader, or second line leader - who's new in their role, is going through. Bring empathy to the table every day. Inspire them to lean into technology: where can we use sales tools to get insight that we can't get because we're not in the office together?

We need to be as much artist as we are scientist as we are psychologist, right?

These stressors don't go away. So as a leader, we need to be there to help get the difficult stuff out of the way, celebrate the good stuff, and let them go faster. And that's in my experience has helped through these virtual times that we're in.

Catherine: One of the things that I've tried to empower my sales managers with is the notion of time management.

I think what none of us really anticipated with COVID is the idea of burnout because, historically, working from home was seen as a luxury. But, during the time of COVID, it was in fact flipped because people were feeling so out of control, the one thing that they could control was what they were doing from a work perspective.

We have unlimited paid time off here at my organization, but nobody was taking it to the point where we were having to force additional company holidays, to require people to unplug. So I'm always trying to tell the importance of time management: there are always going to be 1,000,001 things to do. But where is your time, effort, and energy best served?

And, like Steve said, checking in and making sure that they're making the most of the systems available to themselves, and spending the time that they have in the right places, that are going to make the largest impact for their time investment.

Jim: Yes, managing your time [when working from home] is really important. You're in a new environment, you may have children running around the house. Some people are good at it, regardless of their location, and some people suck.

One thing that we do that I think is helpful is having one-on-ones every week. They’re very sacred, and I try not to ever cancel those.

And we flipped the script a little. We start with results, and then we go to, “What did you deliver?” “What have you added to the pipeline?”. And then if that’s fine, we don't talk about activity. So we kind of gave people a little bit of space to figure out how to manage their calendars, knowing that we were always focused on those outcomes that will never change in sales operations. I think before we were a little bit more activity-focused and calendar-focused, but now it's really focused on the outcome.

My superpower is not compassion. So I have a little note in my book every day to reach out to my team, even if it's just to see how they're doing. I just make sure I’m checking in with them. And sometimes that conversation turns into a half an hour and I have to sit there and listen to them talk about their dog.

It’s funny, I was on a call the other day with a customer and their cat ran across their screen. And they actually said to me, “Isn't it amazing that a year ago, if a cat would have run across the screen or a kid would have run in front of a camera, we would have been mortified as sales leaders and salespeople?” The world's changed a little; I think we give people a little more grace.

Catherine: Grace is a great way to put it.

Universally, I've seen huge returns on making that time investment in members of my team, just them feeling that they are heard, that they are seen, and they are validated.

I do my one-on-one’s slightly differently, where one is really for me and the business, and the other is for them, just for them to have a safe space to talk about whatever matters to them.

Jim: I also think you should keep them accountable, there's that balance of accountability and grace. If they don't hit the numbers, then I earn the right to say, “Okay, open up your calendar, I want to see what you did”.

Steve: Catherine, my one-on-ones are unstructured for that exact reason: if we're going to talk pipeline, that's a pipeline call, right? If we're going to talk about development, that's a team development call - those have a purpose, they have an agenda, we have an outcome we're driving to.

But in one-on-ones with my sales leaders, I don't build an agenda. If it's about your kid, their dog, if it's one of my kids jumping in on a camera, or my dog, Teddy, decides to bark, we talk about any of those things, because it's for them, and about them. There are enough scheduled meetings where it's about the business.

So again, it goes back to that human element. My daughters will routinely jump in on a call and say hi to the team. A year ago, no way. Now, they all know Scarlet and Addison, and my wife will sometimes duck in and give a wave.

Q. In light of current challenges and digital transformation, how can a sales leader balance these, and the need to keep pace with change, while maintaining privacy and confidentiality?

Catherine: I probably struggle in a different area than Jim, where I have a higher EQ than I do an IQ. What I do is highlight when I see a marked change in behavior from an individual, whether it's inflection and tone, during a team meeting; if somebody is a top performer and then all of a sudden, I pick up on subtle changes. I like to address that,, but that's not to say they have to give me that information.

At the end of the day, if I have a member of my team who’s struggling personally or emotionally, I think that part of my job is to do the due diligence and, at the very least, ask that question, without encroaching too much on their privacy or confidentiality.

If it's something that's outside of my scope, and my capability, you know, I then respectfully will say, “Let's make sure we can get you the right help”, because I have found that avoidance is not the right answer. I don't know what all the answers are. But I do know that avoidance is not the right one.

Steve: Jim's very spot on, the business doesn't change, the numbers don't change, we got to deliver those outcomes. But we also need to have empathy in our world. We, as sales leaders, need to make sure we’re taking care of our people.

Because at the end of the day, there are people who we've invested a lot of time, money, and resources into them. So we can get them back into the fold and, to Jim's point, deliver on outcomes.

Jim: As a leader that manages leaders, make sure they know that they can come to you if they have questions, like they shouldn't keep anything to themselves. If they're struggling, they should pull the alarm and get you on the phone as soon as they can. We all probably have some more experience than our sales leaders, and if not, we can guide them to get help from the outside.

Q. How do you aim to transform your sales teams to emerge into the ‘new normal’ without lowering the bar of expectation?

Catherine: For me, it’s not about lowering expectations, but about increasing or maintaining them at the very least - which is pretty core to a sales culture as a whole.

For our organization, because things are opening up, we're now starting to plan things like SKOs (sales kickoffs), kind of the fun side of selling; it's very much a high risk, high reward culture that we nurture in sales.

It’s about “What does this new normal look like?”

Historically, I love the culture and the energy of having people in an office together. However, I cannot make that a requirement, so how can we balance those things out and find a new level for setting expectations, but it's never going to be about lowering the bar.

It’s about really incentivizing and leveraging the collective excitement that everybody's feeling about the ability to be around people again. But also having the empathy and understanding that some people are simply out of practice with those soft skills. We need to build that energy and momentum, but also understand that it's going to seem foreign to people at first.

Jim: I think you have a couple different options as a leader. Number one, is it a systemic problem that isn't going to go away, and you have some tough decisions to make? This is a tough environment - but it doesn't mean that we keep that weight on board. You've got to move quick on underperformers, just like in any other environment.

However, if you've got somebody that has hit a speed bump, or somebody that you can tell is struggling, “We can't change the past, but how do we go forward?” and focus on today as if it was quota zero. Get them focused on some positive momentum moving forward, and not always looking back and saying, “I'm digging myself out of this hole”.

Last Q4, I had a rep who was really behind his numbers, and I said, “Let's just focus on our Q4 number. Forget the rest of the year, let's just focus on what we’ve got to do to hit the number this month or this quarter. And then each month after that we'll build from there”.

So this is somebody that I wanted to keep, but I've also had to terminate some folks during COVID, that probably would have been terminated anyways. It's balancing those two things. I don't think you should carry the burden of keeping someone that doesn't deserve to be on your team. But at the same time, with people that aren't, you just look forward and help them.

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