“Be real.” with Jeff Dickerson

Be real. Everyone has had the storyteller boss. The one who paints the grand pictures, sees the future through rose-colored glasses, and is able to motivate through flowery language. The problem with the storyteller is that eventually, the stories catch up. Time passes and the boss is proven wrong (or worse, thought to have lied or […]

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Be real. Everyone has had the storyteller boss. The one who paints the grand pictures, sees the future through rose-colored glasses, and is able to motivate through flowery language. The problem with the storyteller is that eventually, the stories catch up. Time passes and the boss is proven wrong (or worse, thought to have lied or exaggerated). People’s faith in that leader, and their vision of the future, erodes over time. This is especially dangerous in a crisis where there is already little faith in a predictable future.

As part of my series about the “Five Things You Need To Be A Highly Effective Leader During Turbulent Times”, I had the pleasure of interviewing Jeff Dickerson CEO of DaySmart Software.

Jeff Dickerson is the CEO of DaySmart Software — a technology company that specializes in the design, development and support of simple, powerful, scheduling and resource management solutions for those in the salon, spa, pet and tattoo industries. Today DaySmart offers industry-specific business management software platforms — Salon Iris, 123Pet, InkBook and Orchid — that are leveraged by hundreds of thousands of global users each day.

Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I got my start in sales because I had — and still have — a real passion for people. Building rapport, even with people who may not share my desire to build it, comes naturally to me. In sales, you try to come to people “bearing gifts” and provide them with the solutions to the problems they’re having. Even after leaving sales, this approach has been central to the way I conduct business; finding that place where I can help.

I’ve served as CEO at six different technology companies now. In my experience, I’ve seen organizations struggle to communicate, getting hamstrung by lack of capital or becoming the victim of market shifts. From this, I like to think I’ve learned a lot.

If your ‘backstory’ is the journey of your development, learning and evolving, I don’t think my backstory is over yet. I know I have more to learn, and I do truly love working on a team. There’s an energy when people pull together and try to accomplish goals, and I can’t help but get swept up in it.

  • Can you share with our readers a story from your own experience about how you lead your team during uncertain or difficult times?

It’s hard to imagine a more challenging time for businesses than right now. This global pandemic has been particularly difficult for our customers — hair and nail salons, pet groomers, massage therapists, tattoo artists — all of which were affected immediately and for a prolonged period. At the beginning, we were getting a couple hundred phone calls every day from people in tears. These were business owners on the brink emotionally. They didn’t know what to do next and were calling to cancel their software subscriptions as a way to cut expenses. These are difficult conversations and it’s only natural that our team was taking an emotional beating as the weeks went on.

To give our team the support they needed, I insisted we completely remove the usual metrics we used to measure our Customer Success teams, like abandon rates, wait times and service levels. Managers scheduled ‘mental breaks’ in the day for these reps — an opportunity to take 10 minutes and clear their heads.

What the team really wanted was to help the people calling in, so we empowered them to determine the solution. We gave them the power to solve the problem; no checking with managers, nobody from finance complaining about the discounting. If, in their judgement, the best answer is forgiving someone’s payments for two months — but continuing to allow them to use the software to communicate with their clients or sell products — then that’s what we did. I think giving employees this autonomy, and showing them we trusted them to handle things, made an emotionally intense experience a little more bearable for them.

Did you ever consider giving up? Where did you get the motivation to continue through your challenges? What sustains your drive?

Well, I wouldn’t say I’ve considered giving up. I’m responsible for a lot of people, so that’s never really felt like an option. I admit to getting occasionally overwhelmed by the size of a challenge — I think that’s only human. When you encounter an obstacle or an objective where success looks unlikely, it can be difficult to keep motivated, no question. I suppose everyone has their own driving force. My responsibility to the team is my number one motivator. I do feel that if I get down on what we’re doing, that will spread and success becomes impossible.

I also have two daughters, and their future is important to me. I work to provide for them, but I also work hard as an example to them. If the only thing I pass on to them is a strong work ethic and a healthy respect for the power of diligence, then I’m sure they’ll do well in anything they pursue.

What would you say is the most critical role of a leader during challenging times?

A leader most critically needs to understand his or her team at a time like this. When I build teams, I’m trying to assess the candidate’s abilities, like every other interviewer. I’m also trying to get individuals to share how they see their strengths and whether they can be candid about weaknesses. How will this style/personality affect the performance of the team as a whole? It’s kind of an alchemy. I’m always looking to add something I don’t have, or don’t have enough of. Running a team, especially during times of increased pressure or anxiety, means constantly balancing individual strengths. We all need to be focused on the larger vision too, we should all be steering to the same “north star.”

What you don’t want to do — in my opinion — is led by example. People in positions of leadership have been taught for generations to lead by example. We’re told that the most effective way to get a team to rally and respect our leadership is by being the hardest worker in the room: showing, not telling, the team how to do their best work.

The myth of the “superhero leader” carrying us through tough times is corrosive to the leader because it sets an impossible ideal and its dismissive of the power of the group. Instead, leaders are people who understand how to strategically tap into available resources to keep the team on task when things get tough. Any agile devotee will recognize one of the responsibilities of a “scrum master”: to remove impediments to accelerate the velocity of the team. I believe that’s the best way to lead — help the smart, capable people around you to go faster by getting them what they need. That requires paying attention to their needs.

When the future seems so uncertain, what is the best way to boost morale? What can a leader do to inspire, motivate, and engage their team?

First, I guess predictably, I would say communication. You need to thoroughly understand what your team is feeling, and how they’re coping. This will provide the best indication of how you can “show up for them.” Creating an open dialogue can be difficult — especially over video chat — but leaders need to invest that time. Building this foundation is the only way you’re going to build the trust required to learn meaningful insights.

The second is to strive to provide meaning. A global crisis of this magnitude puts things into a new perspective for everyone. If your company, or an individual’s role within it, doesn’t offer a greater purpose, it’s going to quickly take a backseat in the face of uncertainty. Work with your team to build, or reinforce, that greater purpose. Show each person how important they are to the organization, but more importantly, invest the time to understand how that organization can be of equal importance to them. Whether that’s allowing greater job description flexibility to try something new, or offering learning and continual growth opportunities, there’s always a way to build a greater purpose. A Richard Branson quote I often recount is “Train people well enough so they can leave, treat them well enough so they don’t want to.”

What is the best way to communicate difficult news to one’s team and customers?

Being direct is key. Address something difficult by addressing it head on. Frequently, when you try to “soften the blow,” you create confusion. Your meaning needs to be crystal clear — that’s just effective communication, but with difficult news it is absolutely imperative.

The first step is to properly prepare for the conversation. Can you predict the types of questions that might come from hearing this news? Mapping your responses ahead of time enables you to work through the logic in private, anticipating concerns and avoiding further tension.

The second step is to explain the news, clearly define what is happening. This is how you ensure that you are addressing your team and/or customers with the respect they deserve. This is not the time to “beat around the bush.”

After the news has been shared, the third step is to share the thought process — why this situation came to pass. They deserve the truth and may better accept the news when they have some insight into why this course of action is currently required.

And finally, it is sometimes wise to provide a safe space to air initial reactions. “How do you feel about this?” might provide a controlled environment for venting the initial shock.

This can be tricky as you’re not looking to get into a debate, but you want people to feel heard.

How can a leader make plans when the future is so unpredictable?

The future has always been unpredictable, that’s what makes it the future. Forecasting is the business tactic that we use to “predict” the future — what’s going to happen to our businesses next year. Many very smart people spend lots of time modeling very specific “what ifs.” These forecasts are based on assumptions about what will happen — for a specific edition, of a specific product, in a specific market — eight months from now! Hardly an exact science.

As leaders, we can make thoughtful assumptions about our customers and the market, define the organization’s priorities, outline prototypes, set goals, establish timelines and get ready to take action. Even if these assumptions turn out to be wrong, the point of the exercise lies in the process of planning — not the plan itself. As Dwight D. Eisenhower said, “Plans are worthless, but planning is everything.” The ability to pivot and make new assumptions is going to serve the organization better than bullishly pushing forward with blinders.

Is there a “number one principle” that can help guide a company through the ups and downs of turbulent times?

Clarity and consistency need to become your watchwords when it comes to talking to the troops. Even more important, leaders need to clearly state how we’d like communication to happen. Emphasize your “digital open-door policy” by making it clear how to schedule a meeting with you and other company leaders, and make sure managers prioritize these meetings. This accessibility ensures that everyone is given the opportunity to share, and they know that you value these exchanges.

Department heads should host AMA (Ask Me Anything) sessions for people across the organization. If you haven’t already, create a Slack or a Chatter channel (like #watercooler, for example) just for non-work-related topics. A place to chat and build camaraderie at a time when employees may be missing for more informal exchanges with colleagues.

I also like to focus everyone’s attention on our “why-power.” In contrast to willpower, which requires some serious and exhausting effort to conjure up each day and will quickly burn you and your team out, as a guiding principle, why-power means identifying the end goal and centering every effort to get yourself, your team and your company closer to it with each tough choice and every tradeoff you face ahead.

Instead of “let’s get through this however we have to,” it means saying “let’s get through this because the world needs us to.” That shift in the narrative, focusing on why you’re showing up, is far more reliable for guidance than your willpower. This could be as simple as your mission and vision statements, but it’s a combination of the impetus to jump out of bed every morning as well and the value inherent in your “north star.”

Can you share 3 or 4 of the most common mistakes you have seen other businesses make during difficult times? What should one keep in mind to avoid that?

1.) Focusing too narrowly or trying to maintain the status quo. For example, not looking to the external environment for newcomers in the space. They don’t have the routines and commitment to past insights that incumbents do.

To avoid this mistake, businesses should look to stay focused on end goals and prioritize company values — look at the destination and pick the best road. Don’t look back, we aren’t going that way.

2.) Groupthink. Groupthink is allowing the initial voiced opinions to crowd out others and become the group’s opinion, instead of bringing in thoughts from varying perspectives to come to a more well-rounded conclusion.

To avoid groupthink, give everyone the space to come to their own conclusions and bring their perspective to the table — give everyone room to talk before decisions or opinions are made. Remember that each person is an expert in something with valuable insight to add.

3.) Making a plan and sticking to it too rigidly. In a difficult time, it’s comforting to come to a plan and try to run with it. Without building flexibility into that plan, you may find yourself pretty far down a bad path. Flexibility is a feature in an organization positioned to succeed in uncertainty.

The key to avoiding this issue is similar to #1, don’t focus so heavily on the day-to-day decisions that you lose track of the big picture. Let the destination be the north star and take whatever path feels right each day to get there.

Generating new business, increasing your profits, or at least maintaining your financial stability can be challenging during good times, even more so during turbulent times. Can you share some of the strategies you use to keep forging ahead and not lose growth traction during a difficult economy?

The first strategy is to look to retain existing customers. By looking at the lifetime value of an existing customer, it’s a no-brainer. Customer acquisition costs for a new customer are high because they don’t know or trust us yet — this isn’t a problem for existing customers. It then makes sense to ensure we’re adding as much value as we can to those who’ve already chosen to trust us. Also, it’s much easier to keep a tank full if you first slow/stop any leaks.

As far as acquiring new customers goes, it then becomes about getting extremely clear on your value proposition. If your value proposition isn’t airtight, now is the time to reign it in.

In a recession, it’s about showing that you’re worth their time and money. If you fear you aren’t worth it, how can you become so? Listen to and directly ask for input on your customer’s changing environment — don’t forget, they’re also in crisis and facing new challenges, so what has always worked as a value proposition may not any longer.

Here is the primary question of our discussion. Based on your experience and success, what are the five most important things a business leader should do to lead effectively during uncertain and turbulent times? Please share a story or an example for each.

1. Innovate how we communicate… Communication strategies must adjust to the crisis landscape. We do a weekly “all hands” meeting where I hold court for 15–30 minutes and update the company on priorities and developments. I take questions, recognize new employees, milestones like birthdays and work anniversaries — it’s really just an opportunity for everyone on the team to be in a virtual room together. Now that we’ve managed our way through the first few months of this sea change, we’ll move that to every other week, which was our in-person schedule before COVID-19. In addition to adjusting channels, leaders should leverage new ones — thoughtfully. Zoom has helped us compensate for the absence of face-to-face interactions, but oftentimes we feel compelled to over-schedule or attend meetings. Zoom fatigue is real and was true for remote workers pre-pandemic. Meetings should have a clear business objective before they’re scheduled to avoid the feeling of video meeting overwhelm. We have all heard the joke “this meeting should have been an email” and we’re actively using that as a guideline now.

2. And the way we listen. It’s easy to operate in a way that ignores the circumstances of individual team members — the “we’re all in the same boat” mentality. The fact is that we are not all in the same boat — we’re in the same storm. Some people are managing children, some are caring for elders, others may house someone who has been displaced, etc. The best thing a leader can do is listen. You don’t have to have all the answers — in fact, you likely won’t have answers for every individual situation. However, providing an ear validates the individual as important and worth your time. That validation alone speaks volumes. I do encourage regular one-on-one meetings for each person and their supervisor and use that as an opportunity to keep aligned and to check-in. Direct supervisor interaction is a key role in our management strategy: I think regular one-on-ones with each individual, while that may sound daunting, are crucial in maintaining a motivated team. Things are harder now and that does mean we’ll have to change the way we work. Someone who hasn’t heard from their leadership in a while may feel out of touch with the organization, lose motivation or forget why they loved working here. By touching base regularly, people will feel more included and involved.

3. Combat burnout. For COVID-19 specifically, burnout can be a real possibility for members of your team who “can no longer escape their work.” I have found two things that help address this challenge specifically: First, encourage breaks. Remind your team to take lunch breaks, walk breaks, coffee breaks, etc. just as they would in the office. Even if it’s just to start a load of laundry or cook their own lunch, it’s important they hear from leadership that it’s okay to breathe. Second, encourage learning. Offer learning opportunities to your team — give them a new project or collaboration challenge to keep their work interesting or offer up online resources to expand their skill set or pursue a passion. Invest in your employees and give them permission to invest in themselves. This will yield returns in the long run, through increased job satisfaction and a desire to keep growing.

4. Inculcate your culture. Something I’ve recently been inspired by is the publicly available culture decks from many historically remote or flexible work environments. I’ve seen examples of these public and shareable statements of the culture — detailing exactly what they stand for and spelling out why people would want to work there. I think creating something similar, regardless of your company size, can reinvigorate the culture by solidifying it and reminding everyone what your company stands for.

5. Be real. Everyone has had the storyteller boss. The one who paints the grand pictures, sees the future through rose-colored glasses, and is able to motivate through flowery language. The problem with the storyteller is that eventually, the stories catch up. Time passes and the boss is proven wrong (or worse, thought to have lied or exaggerated). People’s faith in that leader, and their vision of the future, erodes over time. This is especially dangerous in a crisis where there is already little faith in a predictable future.

How can our readers further follow your work?

I’m really not one of those big showy CEOs. I do speak at some trade shows, I’ve done videos for our YouTube channels. I publish on the DaySmart corporate blog, which you can easily find at www.daysmart.com/news

Thankfully, when I do sit down to share my thoughts in longer form pieces, I am fortunate to have found an audience in the trade press serving the verticals in which we operate. So, I do get published pretty regularly in magazines like Salon Today, American Spa and Pet Business — maybe not something you’ll find on the newsstand, but definitely someplace our customers and prospects go for information and education. Those are my people.

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