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4 Lessons on Leading Enablement During Unpredictable Times

The past year was full of changes and, for many, ups and downs. As we move into 2023, some of these challenges may continue, along with an unknown future. 

For example, the Morgan Stanley outlook for 2023 expects low growth levels and the U.S. economy to remain flat. Fortunately, they expect inflation to slow and prices of retail goods and even housing to drop somewhat. 

At the beginning of 2022, Handshake thought they had a solid roadmap for the year. However, economic challenges in the first quarter brought significant changes. So how can enablement teams react, remain profitable, and add value during unpredictable times?

In a recent webinar, Handshake’s Sales Enablement Director, Mark Riley, talked to WorkRamp’s VP of Marketing, Jack Foster, about how enablement teams can adjust during unpredictable times. 

Be nimble

Enablement teams must be nimble. Flexibility is paramount, and you must be ready to adjust your annual plan if the economy dictates.

Enablement has two primary responsibilities: 

  • Onboarding
  • Continuing education

Ideally, these would be balanced, but the reality is that economic conditions often shift the focus. For example, in 2020, during COVID, onboarding dropped significantly, and organizations focused on ongoing education. Mark sees that happening again as we start 2023. 

“This summer, we used WorkRamp from a learning management perspective,” Mark shares. “We put eLearnings in there about recession-related resourcing. Learning from previous recessions. What happened in 2008 and 2009, what our customers were saying, how this recession may have been different. We did role plays; we did live sessions.

And what came out of that was a much more enhanced and equipped team to respond to, ‘Hey, we don’t have budget. Hey, we’re slowing down. Hey, we aren’t purchasing software right now.’ Things like that. And be able to move forward.”

He also noted that the current economic climate uniquely impacts different industries. So Handshake focused on segmenting their training. 

“Then we gave that to the sales reps and equipped them with the knowledge to know, ‘Hey, you’re going into a conversation with an energy company or a hospitality company, they’re probably doing pretty well right now,'” he says. “Versus, ‘you’re talking to a technology company, they might be facing layoffs, they might be dealing with a freeze in hiring.’ Whatever it is.”

When your enablement team can tailor your approach to what’s happening in the market, you’ll maximize your impact.

Read More: How to Stay Competitive in an Ever-Evolving Market

Prove your worth

Enablement professionals may be tired of this message, but it’s a vital way to protect your team members and resources. Unfortunately, teams are shrinking in the face of economic pressure. As a result, proving your worth is more important than ever.

Mark emphasized the importance of having specific metrics and goals that serve as your team’s North Star. For Handshake in 2022, the key focus was increasing contract value size. The team broke that into two strategies: connecting with the right audience and selling additional products. 

From there, Handshake’s enablement team built training to support those goals. It was successful, allowing them to point to significant increases in average contract value in Q1 and Q2 as concrete proof of the team’s value to the company.

“I always think for enablement professionals, if you can have one or two key North Star metrics that guide you through a year, you have a couple different segments or buckets coming from that, maybe four or five,” Mark says. “And then the specific learning initiatives, maybe 10 to 12, mapping into months throughout the year. So that will cascade downward or upward into those North Star metrics.

And so when we think, ‘OK, how do we maintain? How do we keep our value? How do we say this is a business-critical function?’ When you can give numbers like that, and you have those North Star metrics, it’s a lot easier to go to a board, to go to a CEO and say, ‘here’s your worth, here’s what we’re working on.'”

Internally, it’s all about being visible. Enablement team members should answer questions on the company’s Slack channels, lead all-hands meetings, and have enablement sessions. 

It’s also important to talk to each department in a language they understand—in discussions with the product team, you talk about adding more value to the product, and in meetings with the sales team, you talk about ways to increase deal velocity. 

Read More: Data-Driven Sales Enablement: Track, Measure, Improve

Think big picture

Mark’s third lesson was how enablement teams that focus on the big picture will be more resilient and successful. 

It’s crucial during tough times to focus on the things that don’t change. Your organization’s mission and culture shouldn’t change; they should serve as the foundation as you move forward. 

Mark shares that many organizations overreacted to the early months of COVID-19 in 2020 as the economy shut down. In the uncertainty, some companies reduced staffing right away. By the end of the year, those same companies were struggling to find employees and keep up with demand. 

Keeping your eyes on the big picture and the company’s mission from a decade-long perspective can help you avoid these overreactions you regret.

Jack summarized, “Don’t go switch everything you’re doing. You need to be nimble for your first point. And be reactive and flex into things. But lean into what you’re good at and your strengths during these times.”

Finally, Mark advised enablement teams to focus on goals unrelated to external economic conditions. After all, you can’t do anything about the stock market, but you can focus on sales team retention and how often you hold sales enablement sessions for various departments. 

When you do that, the enablement team will continue positively impacting the organization, regardless of the economic situation. 

Control what you can control

Keeping your enablement team focused on what they can control is vital despite unpredictable times. 

The first step is to look at what you’re doing now that’s working well. Then, you’ll want to maintain and build on that. Then, consider what you can do to use the tools you have more effectively and efficiently. 

For example, in 2020, Handshake began using WorkRamp as a continuous learning platform instead of simply an onboarding program. Using the libraries and integrating example calls into WorkRamp, they could improve their capabilities without additional investment or resources.

Continuing current enablement programs can also help employees maintain a sense of normalcy and may lead to growth in a challenging economic environment. 

Every enablement team can also control whether they have regular enablement sessions, how prepared they are, and whether they continue to document and share best practices—especially for the sales team. 

“I think that that piece of things, of maintaining that sense of camaraderie and looking at the programs that are going well, and augmenting them, can be extremely helpful during this time.” 


-Mark Riley


Learn more about how your enablement team can adjust during unpredictable times. Watch the on-demand replay.


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Anna Spooner

WorkRamp Contributor

Anna Spooner is a digital strategist and marketer with over 11 years of experience. She writes content for various industries, including SaaS, medical and personal insurance, healthcare, education, marketing, and business. She enjoys the process of putting words around a company’s vision and is an expert at making complex ideas approachable and encouraging an audience to take action. 

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