4 Predictions for 2021: Coaching, Leadership, and Developing Sales Teams for Growth

January 21, 2021

Sara Howshar

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This week’s Weekly Briefing was marked by many new things. A new year, a new US administration, and a new sense of bold leadership for 2021.

Jim Benton was joined by Justin Clifford, the Head of Commercial Sales at Lessonly. They discussed the immense energy entering into this new year, and have dedicated this episode to the importance and role of leadership in the coming year.

“It’s a new quarter, a new month, a new year,” said Justin, “But yesterday definitely added new levity for me.”

Thinking about leadership and how essential it is right now, SKOs will help set a new tone for the next year.

“The last year has been tough,” Justin said. “We learned a lot about ourselves and our businesses. Now’s the time to build on that.”

Justin runs the Commercial sales team at Lessonly. As training software for companies, they have several guiding principles that make their way into their product and their own teams.

“In all honesty, in mid-April things were looking pretty bleak. And this team turned a corner in September. We’re very fortunate to be a software that works well in a remote environment.”

Now that we’ve made it to 2021, it’s time to look forward.

Jim continues to ask the question that fuels Chorus forward: How do we help people be the best version of themselves?

I have seen success in picking up the phone and asking people how they’re doing. And I say success because really good connected conversations happen there.

2021 Prediction 1: Revenue Leaders will Find New Ways to Keep Spirits High #

Chorus data shows that burnout mentions are up 32% compared to Q1 2020. The question is: How do leaders proactively combat burnout and keep their teams engaged?

Justin admitted that it’s difficult for him. “The biggest takeaway for me is that everyone is different. We have different needs.

One thing that clicked for me last week was after two conversations I had back to back. One AE said ‘I need more open meetings with everyone on and no agenda.’. And the very next call was with another AE who said they needed agendas and can’t have any more open-ended meetings in their life.’”

Finding new ways to connect and build better relationships is key. “We can’t go and have margaritas like we used to,” Justin added. “So we have to work through it.”

So what can leaders do to ignite the energy needed for their teams to thrive?

“Keep that long term scope,” said Justin. “Let’s worry about today together, and build momentum around the future.

Day to day can be drastically different for people. I have seen success in picking up the phone and asking people how they’re doing. And I say success because really good connected conversations happen there.”

You have to keep it fresh. It feels like there needs to be a full time dedicated resource for [culture].

Too Many Happy Hours? #

Strategies to encourage connection within your team likely looks different than it did even a few months ago.

“One of the jokes has been around the team happy hours,” said Jim, “because they’re definitely highs and lows.”

Justin agreed. “There’s lots of trial and error there. We had a lot of virtual open-ended happy hours, then we moved towards themes. I started looking into new ways to do this... But it’s tough. You have to keep it fresh. It feels like there needs to be a full time dedicated resource for [culture].”

Jim agreed, “We’re all in the same boat in this regard.”

SKOs are a Pivotal Event for Re-energizing Tired Teams #

Justin shared his excitement for Lessonly’s first SKO coming up. “This is our first true SKO. Our Head of Enablement is brilliant at this and has done this many times, so we’re lucky to have her. We’re going to have it throughout the course of a week - it’s going to have sessions, workshops”

Chorus is having a yearly “FKO” (Full Company Kick-Off) soon as well. “We’re really excited to see what comes from it,” said Jim.

I almost view the office being the culture and community spot, not necessarily the work spot.

Prediction 2: Revenue Leaders Will Evolve Team Structure and WFH Processes As Offices Open #

Last year’s work from home pivot was thrown on us. But this year, we have an opportunity to build up and around ever-changing circumstances. Many offices are adopting hybrid models based on flexibility. For example, an office where teams are asked to spend 50% of their time there and 50% of their time at home.

An underlying complexity in WFH models is culture. How are leaders planning to infuse culture into a hybrid or fully-remote workforce?

“It comes back to the individual,” Justin said. “Some need the office, some work best at home. So it’s important to understand what people need and provide that.”

“When you think about the offices opening up,” said Jim, “I think flexible is the key point.”

The Office is for Culture, Home is for Work #

“I almost view the office being the culture and community spot, not necessarily the work spot,” Justin said. “This is going to be the place where people gather. This is really what our People Team is working on with Leadership. How to build that - there’s going to be a lot of trial and error to be there.”

“When the world opens back up, I personally want to work with people again. But I also want the flexibility - so maybe the days are different,” said Jim. “But I want to collaborate in person.”

And for leadership, it’s important to spend time with your team in a flexible, unscheduled way.

Justin agreed: “Walking the halls - that face-time - is really important for leadership as well.”

Build a solution that’s custom for them within the framework of our features. This drives huge success.

Prediction 3: The Most Successful Teams will Double Down on Skills Coaching #

When we think about onboarding and building our best teams, coaching is top priority. However, as in past years, the coaching activity took a steep drop off in Q4 as teams try to close as many deals as they can before year-end.

This brings into focus two different approaches to coaching: Skill Coaching and Deal Coaching.

Justin heartily agreed with this prediction.

“We’ve been working on skills related coaching for a year and a half,” said Justin. “It is really hard to get started. You have to define these skills, hire for them, train for them…”

Justin shared how he and his team have mobilized their coaching to address long term skill-building.

“Understanding what metrics you can move by highlighting these skills is essential. We work on one or two skills per quarter with an AE. We identify the metric and tie it to a benchmark, and there’s a weekly cadence on coaching. We’re not focusing on deals at that moment but the overall skill.”

“We can get out of the spreadsheets and into Lessonly,” he said. “Which will be a big move in getting out of deal coaching and into skill coaching.”

A particular skill they’ve focused on is “Building a Solution for a Problem.”

“Oftentimes this skill becomes a catalyst for big success for our AEs. There are always features,” he said, “but unless you understand the problem, the desired outcome, and the timeline, you’re just throwing features at them. So instead, build a solution that’s custom for them within the framework of our features. This drives huge success.”

And of course, there are many sub-skills within this such as listening and asking the right questions. And those can be addressed within the weekly coaching sessions.

I’m excited to bring the energy back with leadership. Let’s go make it fun.

Prediction 4: Winning Teams Will Rally the Company Around the Customer #

While we’re not with our customers at events and such, customer-centric sales have been a focus. Our data shows that there has been a 41% increase in CSMs joining AE meetings.

“This stat validates our customer focus,” said Justin. “We’re focusing on creating the best solutions for our customers. We want to be business partners, not just click-to-purchase.”

Revenue orgs are getting better at being true business partners.

“We are finding that more people are involved,” said Jim. “CSMs are getting involved earlier. We want to make sure we deeply understand them earlier and help where we can.”

Understanding our customer's ties into the first prediction 1: How do we invoke the spirit of excitement and collaboration? “We want people to connect and have meaningful conversations,” Jim added.

And that brings us to our unofficial Prediction 5: This year is going to be about making things fun.

“I’m excited to bring the energy back with leadership,” said Jim. “Let’s go make it fun.”

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