HR & Leadership

Leadership Advice in Times of Crisis—from Highspot’s Oliver Sharp and Robert Wahbe

June 23, 2020

Unprecedented. Yep, there’s the official word of 2020.

While some industries have been harder hit than others, leaders in every industry face unprecedented challenges on multiple fronts including overall strategy, day-to-day management, forecasting and the wellbeing of their teams (and themselves).

It’s a lot.

I recently caught up with two of the best software leaders I’ve ever worked with: Robert Wahbe and Oliver Sharp from the revenue enablement platform Highspot. As a board member at the company, I’ve been impressed with their leadership during the COVID-19 pandemic, and I wanted to understand how their experience from prior crises has guided their response to today’s challenges.


Oliver pointed out early in our conversation that while many of us have survived multiple economic downturns and recessions, today’s crisis is unique given the public health challenges and required adaptations associated with the underlying pandemic.

“Human beings are social creatures who take comfort from each other in times of stress,” he said. “The nature of a pandemic means we’re physically and socially isolated from each other. That’s a really weird and different dynamic than any I’ve experienced before.”

I couldn’t agree more.

There are timeless leadership lessons and best practices that we can draw on today. But we also need to navigate the unique dynamics of a global pandemic and develop new best practices. While Robert and Oliver’s advice was developed in the context of a software startup, these are widely applicable leadership strategies that can be applied in any industry and with any team.

Communicating effectively: Sharing both the plan and the strategy

“In a crisis, people want to know what’s going on,” Robert said. “That’s why what, how and when you communicate matters more than ever.”

The basic rule of thumb: Communicate early and communicate often. As Robert said, you really can’t over-communicate in this kind of environment, and “enough” communication is often a lot more than you’d expect.

Part of the challenge is that in moments of crisis, people don’t listen as well. They often miss the nuances of what you’re saying, and sometimes even the broad brushstrokes. This is why repetition and clarity are important communication strategies for leaders at all levels. People have a lot on their minds right now. It may take a few times before something you said can cut through all the noise.

“What, how and when you communicate matters more than ever.”

Robert advocates strongly for communicating not only what’s happening, but why it’s happening. “People naturally communicate the plan,” he said. “They might say, for instance, that there’s going to be a hiring freeze—a common plan right now. But you also have to communicate the strategy behind that decision. Why are you doing that? How did you make the decision?”

Related read: Leaders Eat on Camera—Advice from 10 Years of Leading Remote Teams

People need to know what’s going on, but having the “what” isn’t enough. “Even more, people want to understand why things are happening so that they might be able to predict what might happen in the future,” Robert explained. “If you give them both the why—the strategy—and the what—the plan—people do much better.”

At Highspot, leadership communicates at least twice per week with the whole company about both the strategy and the plan. This helps keep their team aligned as they navigate unfamiliar territory together.

Adopting a strategy of optionality: Give yourself room to maneuver

Another key strategy that Oliver and Robert embraced is optionality. This strategy is very different from standard business procedures.

“In more normal circumstances, you have your strategies, and that comes out with a forecast and a set of operating principles,” Robert explained. “You map those out over the year, and then you execute against them. Standard business 101. Optionality is more about how to have a plan that says you’re not going to have a plan. That’s a hard thing to do.”

Optionality is about keeping your options open so you can react with more flexibility to things outside your control. A big part of this is being careful about one-way versus two-way doors.

“Two-way doors are things you can undo,” Robert said. “For example, if you’re going to sign a vendor contract for a very important piece of infrastructure, a two-year contract is a one-way door for two years while a month-to-month contract—while it might cost you more—is a two-way door, a decision you could undo.”

To put optionality into motion, Highpoint developed a simple matrix to show the possible macro environments, which they call economic ripple, economic recession and economic reset. They look at possible scenarios and outcomes in these three environments not just for this year, but also for the next year.

“When you’re thinking about your overall plan, make sure you’re understanding the implications not only for this year, but also for next year,” Robert cautioned. “This is especially if you’re in a B2B business with long lead cycles because, often, what you’re hiring for in a given period is not for the current period, but for a period two, three or four quarters from now.”

The general idea is to make predictions based on what could happen in each macro environment and then develop plans based on optionality. The decision-making process about whether to go with Plan A, Plan B or Plan C is also set up on a framework.

“Knowing when to go from one plan to another depends on what you put as your key triggers in each macro environment,” Robert said. “For most companies, a key indicator is the ability to achieve revenue targets. So, if you said that in the economic ripple you were going to achieve 80% growth, and then you find after a few months that you’re not hitting that goal, you know it’s time to move into a different column.”

Whatever scenarios, key indicators and triggers you define for your optionality strategy, it’s critical to reevaluate the matrix frequently. Robert and Oliver recommend monthly if possible to make sure you’re staying on top of what’s happening.

“The truth is, we have no idea how to forecast in this environment,” Robert admitted. “So don’t spend a lot of time trying to forecast. Instead, put every ounce of that energy into helping your business, telling the right story for an economic downturn, changing your COGS, changing your product portfolio—whatever you need to do. Putting your energy into these efforts helps you maintain optionality.”

In short, optionality gives leaders a bit of leeway and a little bit of grace because you don’t have to be the most prescient person on the face of the earth to pick the exact right scenario. Instead, you can have all the different paths and a set of rules that help you pick which path is best for which situation.

It’s like working with a chessboard on which every square is playable as opposed to a dartboard on which your winning hits are limited and you just have to hope you get it right.

Engaging customers: Being human and increasing value

There is no question that everyone’s mental state and health have been affected by what we’re all going through collectively and individually. This has been tough on many levels, and no one is exempt from the discomfort, anxiety or grief.

With that in mind, I asked Oliver for some advice on how to engage customers in such a fraught time. He sees two components that must be addressed: the human component and the value component.

“On the human side, one important thing is to embrace that the people you’re working with are under a lot of pressure,” Oliver said. “They might be in a pretty fragile place, so you need to be even more empathetic than usual. You need to be there to support them. It’s like the Maya Angelou quote: ‘People will forget what you said, people will forget what you did, but people will never forget how you made them feel.’”

Oliver suggests that each time you enter a conversation with a customer, focus on how to engage them so they walk away feeling better, more supported and more confident.

“This is important not just because it supports your customer, but also because it sets the foundation for an even closer and better relationship on the other side of all this,” Oliver added. “Remember, your customer may be going through layoffs, their job might be at risk, they might be worried or anxious, they may be under a lot of stress. The human side is really important. It comes first.”

The other aspect of working successfully with customers has to do with making sure people are getting as much value out of your product as possible. This might look like teaching them best practices or going deeper on ways to leverage your product. Mostly it’s about being as helpful as possible.

“If you’re a SaaS product, it’s very possible that your customers are relying on you more than ever at this time,” Oliver says. “That’s certainly true for us because a lot of what we do—helping convert information to field-facing teams—has been cut off by social distancing.”

Helping customers take full advantage of your product makes their lives a little less stressful, and that goes a long way right now.

Oliver also pointed out that—if you’re careful to be empathetic—there are sometimes opportunities to push the boundaries.

“During times of transition, you can challenge some of the conventional wisdom and really move the way a customer is leveraging your product,” he says. “They might be willing to change the way they do things in ways they wouldn’t consider under normal circumstances.”

Just be careful about how you approach and manage these kinds of conversations.

Supporting your team: Practicing empathy and individualized response

While providing additional support to your customers might come naturally, it’s also critical to think about how to support your employees. As Robert pointed out, this requires that you tailor your support to each person.

“Remember that—whether you’re a small company or a big company—the people on your team are potentially experiencing this radically differently,” he said. “You really do have to individualize your approach to make sure that everyone is getting the right kind of communication and the right kinds of conversation.”

He goes on to explain how different the situations can be. “You might have early-career people who were doing great and then are all of a sudden stuck at home with four roommates, a lousy internet connection, and having to manage business meetings out of the bathroom. On the other hand, you might have someone who lives alone (a different kind of stress) or someone who is homeschooling their kids on top of their work responsibilities.”

“Everyone feels more fragile and tired. Be empathetic. Even if you have a great situation with your home office and setup, this still feels harder.”

In short, there’s no one-size-fits-all situation or corresponding support mechanism.

Oliver added that all this upheaval also means things that work under normal circumstances might not work so well in this moment.

“People are more fragile than usual,” he says. “So be more careful and thoughtful. If you’re used to pushing people in a certain situation, maybe this isn’t the time to do that. You can’t expect everybody to work all the time through this.”

In other words, cut people some slack.

Robert agreed, “Everyone feels more fragile and tired. Be empathetic. Even if you have a great situation with your home office and setup, this still feels harder. Remember that what you experience might not be what your team is experiencing. Create the space to have that conversation. I think that really matters. Help people understand how they can support other people left, right, up and down.”

Related read: How Successful Remote Teams Manage Mental Health

Robert also pointed out that helping people support others on the team is especially critical for managers.

“Creating a safe space where people can say that they need to take care of homeschooling or an elderly parent really comes down to a lot of manager enablement and support,” he explained. “You have to make sure your manager community is doing great so that your employee communication is great.”

And just like with customers, you should think about how the time you spend with your employees makes a positive difference in their lives. As Oliver put it, “Ask yourself if you’re meeting the bar of making a difference, and if you’re meeting it up, down, sideways? It’s a really good question to challenge yourself with. You won’t always rise to it, but you should always try.”

Taking care of yourself: Setting up support networks and pacing yourself

Finally, there’s the matter of self care. It’s easy to overlook this one when you’re in a leadership position because you feel responsible for taking care of everyone else.

But if you burn out, you’re not going to be any good to anyone, so it’s critical to figure out how to sustain your own mental health and stamina.

“In a crisis, the same things you should normally do still apply—they’re just intensified,” Oliver said. “For example, one of the core leadership principles is that the leadership team is the first team. You are there for each other. You support each other. You can be vulnerable with each other and talk about your struggles in a way that’s really not appropriate to do with your team. Leaning on each other is really important.”

Robert added that it’s important to pace yourself. “Good leaders work hard, and they are working even harder now because they’re managing their company through a once-in-a-century crisis. That’s okay, but whatever your work/life blend and balance is, you’d better be doing it in a way that you can sustain. Burnout is a key thing you have to manage against, both for your team and for yourself personally.”

Keeping the big picture clearly in sight: Identifying opportunities and planning for the future

While the day-to-day might seem bleak and looking ahead might feel like peering into a thick fog, all is not doom and gloom.

Even in times like these, there are opportunities to not only survive, but to thrive. And when you’re building a company to last, you need to take that long view so you can identify these opportunities and take advantage.

Times of adversity are, for example, a great chance for you to really step up for your customers in ways that make a real difference and strengthen your relationships.

“The only thing you know about an economic downturn is that it will be followed by an economic upturn.”

You can, as we already mentioned, challenge the conventional way of doing things and potentially create new inroads to different and more expansive kinds of engagement. You might also be able to recruit some really great people. Most importantly, according to Oliver, you can invest in your core differentiators and really build them up.

“You want to put yourself in a position so that when we all emerge from this and we’re back in a more conventional environment, you have what you need to get to that next level of competitiveness.”

Finally, Robert added, “Remember that this is likely a marathon, not a sprint. Even when we go back to work, it might be in periodic waves.”

This is both a mindset and a tactical consideration. You have to plan for how to continue running your business, and also how to keep your and your team’s morale up.

The good news? This too shall pass. “The only thing you know about an economic downturn is that it will be followed by an economic upturn,” Robert says. “You have to be optimistic. At Highspot, we say that we’re going to manage through the downturn and invest into the upturn.”

Oliver agreed, citing the Stockdale Paradox as a concept that can be very helpful in times of distress and uncertainty. “The concept was named after a Vietnamese POW who was imprisoned for a long time,” Oliver explained. “When asked who makes it through a brutal crucible experience like that—much worse than what most of us are facing—the POW said that the people who got through the ordeal were long-term optimistic and short-term realistic. So, the people who think every helicopter might be their rescue were constantly disappointed. It would break them. And the people who gave up on ever getting out lost their spirit. The people who made it through believed they would ultimately make it thought, but acknowledged that they couldn’t expect things to get better anytime soon.”

It’s a smart, level-headed approach to a situation like the one we’re in now.

To hear even more advice from Oliver and Robert, listen to their full episode of the BUILD Podcast.

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