How to lead sales teams through market and organizational change

Posted November 6, 2020

headshot of lady smiling

By Cari Murray

Senior Editor at Outreach

We all know change is a constant in business and in life. And now, there’s never been a more difficult time to be a leader. It’s a major balancing act.

To get a sense of how leaders at other companies are adapting to this new environment and leading their teams through all the market and organizational change, David Rubinstein, Vice President of Sales at Outreach, recently sat down with Lakendra Davis, Assistant Vice President at AT&T, at our Unleash Summit Series.

Read below for highlights from their conversation about successfully and empathetically leading sales teams through organizational change. (Note: We’ve condensed and edited the original discussion for this post. You can watch the video or listen to the complete interview on

Based on what’s happened in the world, how have you changed your strategy?

Lakendra: I run a fairly transactional business that is heavily focused on the small business space, such as the mom-and-pop businesses of the world, professional services, restaurants, bars, etc. Typically, we move deals through a sales cycle really quickly — we often go from discovery to deal closure inside of 30 days. And so, we haven’t historically spent a lot of time reflecting on our sales wins. We just focused on building our funnel, keeping our activity going, and continuing to move things through the sales cycle.

However, after COVID-19 hit, we had to be more deliberate about looking at our sales wins and trying to understand the profile and nuances associated with the type of customers who were buying. As we uncovered those wins, we looked into our market and tried to find more customers like them. So really, we pivoted from being transactional to being far more strategic.

We also doubled down on learning and facilitated more discussion with subject matter experts on some of our solutions that have become mission critical in this new environment. For example, as companies have sent employees home, they’ve had data and applications running over their employees’ private home connections, and they’ve had to make sure those endpoints are secure. A lot of businesses hadn’t thought about that. We made sure our sales team felt very comfortable having those conversations because those weren’t typical sales in our more transactional environment. So, we’ve absolutely doubled down on learning, and we’re spending more time educating the field.

How do you keep morale up? Because it’s not easy and it’s a grind out there. And every transaction requires more effort than it did six months ago.

Lakendra: I think leaders have to understand that they absolutely have a role to play in what happens to their team and company, and that they set the tone. So, as a leader, even on the days that are challenging for you, you’ve got to get up and bring the energy, bring the enthusiasm for your team. It will not trickle down if it doesn’t start with you.

A few things I’ve personally been doing to keep morale up include:

  • I’m always reminding my team that they have to take care of themselves. They have to decompress. They can’t stare at a computer all day.
  • I’m doing a lot of ad hoc one-on-one engagement. For instance, I may just scan my org list and say, oh, let me call Dana. The first few times I call Dana she may think maybe she has done something wrong. But then word spreads that no, Lakendra, was actually just calling to say hi, check in, and see how you are doing.
  • I get our entire team together every Wednesday at 4 p.m. on video. We all bring our own drink and do a virtual toast and sip. It might be something as simple as we survived another week or cheers to a successful month. Then we spend about 15 to 20 minutes on some sort of learning or fun activity such as Trivia, Rebus games, etc. At the end of the call, I as the leader, mandate that everyone close their computer and go do something else.
  • I share when things are tough, but even when things are tough, I’m still doing the work; I’m not asking my team to do anything that I’m not doing. I let them know it’s hard to keep going if you don’t see an immediate impact of what you’re doing, but you have to keep going.

What is the hardest part for you about being a leader in today’s environment?

Lakendra: In the beginning, managing expectations not only for my team, but for myself was difficult. I was still very much holding myself accountable to our original business plans and kind of business-as-usual level results. I wasn’t giving myself grace or extending that grace to my team around the reality that business-as-usual was gone. It was out the window. Because in the beginning, everyone’s production was impacted.

...To get through all that, we had to change how we were defining success. We had to determine: What does a win look like in this environment? And so, we elevated our focus on effort, not just impact. We had to become a lot more focused on the inputs, such as managing behaviors around sales prospecting activities, phone calls, emails, and funnel growth, etc., and celebrating those types of inputs. We also started leveraging Outreach to help us be more strategic from a prospecting standpoint and identify those clients that we could put in a sequence and guide them through an experience.

How has this experience changed you as a leader?

Lakendra: Gosh, I think just the level of empathy I have and expressing that empathy more consistently and openly. I’ve always been an empathetic leader. I think I’ve done that more privately than publicly though. I also think I’m more flexible now in how and where people show up, the type of adjustments that I make for my team, and in my work style. I was historically a leader who wanted everyone to be in the same room if we were having a big meeting or a big blitz. I wanted that energy. But I’ve realized I can get that virtually. We all keep talking about when things go back to normal. But things are never going back to normal, right? We all just have to keep moving forward and continually adapt and evolve what we’re doing.


Read more

Discover the Sales Execution Platform
See how Outreach helps sellers close over 2 million opportunities every month.