7 Things Most Likely to Keep Business Leaders Awake At Night

Dr. Julie Tofilon, Contributor
Monday, May 24, 2021
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7 Things Most Likely to Keep Business Leaders Awake At Night

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Tags: #leadership #professionalgrowth

Have you ever wondered if you're the only one who cares about something, struggled with something, or been through something? No matter your personality type, temperament, strengths and weakness, it's part of our humanity to not want to be "weird."

Our thoughts, feelings, experiences, concerns, and even our sense of purpose seem validated and confirmed by having something in common with others.

While it's comforting and encouraging to have someone empathize with us, we truly feel affirmed when someone identifies with us and declares, "Me too!"

Business leaders feel this same need for validation and confirmation in shared interests, concerns, and stories. With that in mind, I interviewed a cross-section of business leaders and asked them three questions to get some insight into what really matters to them.

  1. What issue (or issues) keeps you awake at night?
  2. Name 1-3 leadership skills you want to develop in the next 12 months to make you a more effective leader.
  3. Name 1-3 character traits you want to develop or improve to become the kind of leader others want to follow.

The leaders in my informal survey group included both men and women of various ages and experience across a spectrum of diverse cultures and races. Some work in larger corporations and some in start-ups.

Seven Sleep-Depriving Issues

Here's a quick rundown of the seven main issues that keep these business leaders awake at night:

  • Planning — shorter-term, financial, and tactical
  • Long-term strategy
  • Dealing with market changes due to Covid
  • Working remotely/working from home as a result of Covid
  • Staff retention and team cooperation
  • Anxiety over decision-making (often, but not solely, due to the effects of Covid)
  • Funding for female entrepreneurs

One leader in the logistics industry, Max Kohanyuk, had this to say:

"I tend not to stress about the issues at work. It's just work. We will get it fixed! Stress only clouds people's judgement. As a rule, the challenges usually are attributed to People, Finance, Technology, or Processes. Personally, I do spend of lot of time preparing, analyzing, and assessing possible contingencies. My goal is to have no stone unturned before I make a decision. I always ask myself the following question: ‘Have I done my due diligence?'"

In other words, he doesn't worry about work issues, but recognizes that any challenge, be it professional or personal, can affect his mind, mood and performance if not dealt with properly.

Another leader, Edward Teal, of Value Real Investments, LLC., expressed the main thing keeping him up at night is "future financial planning and looking at how to grow my business. I don't really have any type of business problems that keep me awake at night."

A female leader strongly stated her big issue is simply, "How do I break the funding barrier as a Female Founders & Female Entrepreneur?"

Loran G., a strategy executive in e-commerce, says his greatest concern directly relates to the COVID pandemic and all the upheaval it has caused in his particular industry:

"In my business of e-commerce and changes of consumer behavior lately, due to Covid, it's a double-edged sword — more people shopping online, but the business model was not set up for it to be so important so fast. People are not trained the right way, stores are not balanced, etc. So they're making very quick changes to strategy and I'm a technology vendor that sells software to those stores. I have to understand their strategy to make my own — their quick change means I have to change that quick, too. Am I too slow or too fast? I'm not sure if I'm pushing my team fast enough or trying to make too many changes too fast. All the upheaval in the industry has caused me to be a victim of their change — it helps me but it hurts me."

In other words, Covid has created both new opportunities and a lot of havoc in his business, with a lot of risk and loss of control in his own leadership. Much like a huge wave rolling in from the ocean, to a surfer this can carry exciting possibilities but also potential for wiping out. Loran feels both of these, along with the strong discomfort any leader feels when circumstances that affect them get beyond their control.

Leaders have expressed varying degrees of anxiety caused by Covid's effect on the economy, their industry, and the decisions they have to make because of that.

A few leaders stated that areas related to long-term strategy keep them awake at night, as they try to plan and discern how to make the right decisions now for their future. For example, Darryl Wilkerson, in Aerospace, Defense and Intelligence, said what keeps him thinking is "Long-range strategies... I worry what am I failing to do right now, today, that's going to constrain the organization in 3-5 years?"

Then there's a couple of younger leaders who are dealing with the challenges of working from home with so many distractions, mainly their kids at home with them. It's a stretch for these folks (mostly men) who are used to working outside the home in office environments that are more conducive to business productivity. They find it difficult to concentrate and produce results in what has been their play/family/kick-back space.

One top leader deals with frequent staff-turnover and relational tensions in his company, including lack of cooperation and employees dissatisfied with management. This confirms the adage that "People don't leave jobs. They leave other people."

Diving Into the Details

Considering that both skill and character in leadership strongly impacts effectiveness and success — the ultimate goals in any organization — I asked leaders about both of these issues. Leaders know that the more they improve in these areas, the less headaches and insomnia they'll have.

When asked "Name 1-3 leadership skills you want to develop in the next 12 months to make you a more effective leader," responses included:

  • Active listening
  • Time management
  • Slowing down so as not to get ahead of their team
  • Communication skills to understand and be understood better
  • Creative thinking
  • "Staying out of the way" — discerning when staff should make the decisions
  • Better planning skills, especially weekly
  • Providing constructive feedback in an appropriate and timely manner — one leader expressed how he doesn't like delivering negative feedback or challenges but knows it has to be done sometimes, the sooner the better.
  • Organizational tools and time management — especially as a remote worker and team leader — because "the rhythm of how and when to work has changed. Tools and planning haven't kept up. I feel unease that it's not quite right."
  • Product knowledge

Among these, listening, communication skills and time management were the most commonly expressed needs for improvement.

When asked, "Name 1-3 character traits you want to develop or improve to become the kind of leader others want to follow," responses included:

  • More empathy, i.e., a better management of people's needs vs. corporate goals
  • Becoming a better listener (as opposed to talking too much)
  • More cheerful — enjoy and celebrate wins
  • More patient with others
  • More thoughtful of others
  • More openness and transparency
  • Finding more joy in daily work
  • More of an attitude of gratitude — for example, one leader said, "…to pause to reflect on how I've been so blessed... to God for the great opportunities. And it helps others want to follow because I can pull the best out of them when they know how thankful I am for the work that they do."
  • More receptivity to new ideas — "More open to new perspectives, ideas and changes during this time that's been so hard on everyone." The leader who said this also felt that having more gratitude would also make him more open.
  • Living up to commitments — as one leader put it, "If I say you'll have this by Tuesday, but don't get it to you until Thursday, I could have done that better."
  • More kindness
  • Better emotional-regulation/self-control
  • Less perfectionism

For character-improvement, leaders' responses clustered in the areas of greater concern for others; attitude adjustments (joy, gratitude, etc.), and keeping commitments.

The Interface Between Challenges and Solutions

Putting this all together, let's examine the interface between issues keeping business leaders up at night and solutions related to improving both competence and character.

1. With the major concerns around planning — financial, strategic, etc., help would come through better planning skills, time management, organizational tools, creative thinking, and empowering staff with more decision-making.

2. For long-term strategy, solutions would be similar to those mentioned in the previous point.

3. In dealing with market changes due to Covid, it would definitely help to stay on pace with the team, be more receptive to new perspectives and ideas, live up to commitments, and find ways to reduce stress, such as relaxation, exercise, music, prayer and meditation.

4. With the challenges related to working remotely, particularly at home, also mainly due to Covid — anything that helps these leaders concentrate, maintain productivity and high performance, and keep good relationships with their family will be key. Organizational tools and time management are helpful, of course, but this is where character really counts. For example, practicing patience, kindness, self-compassion, thoughtfulness, and empathy not only with team members but family members as well.

Since concentration and productivity are directly related to mental well-being, focusing on joy, emotional regulation, gratitude and less perfectionism will not only make them feel better, they'll also perform better.

5. Regarding staff retention and team cooperation issues — people leaving, passive-aggressive behavior, and hostile attitudes toward leadership that sometimes lead to hostility within the team (all derived from the same core malady) there can sometimes be a lack of character and maturity in leadership. Yes, character matters. Some leaders recognize their need for more patience, self-control, empathy, thoughtfulness, etc., but some don't.

The ones that do have already taken the first and biggest step toward solving their people and team issues by owning their part and expressing a willingness to change. The ones that don't, need to examine their own character and leadership style as the common denominator in all the trouble with staff. From here, they can work on it with help, support, and accountability.

6. Leaders can overcome anxiety about making the right decisions by involving their team in decision-making, developing contingency plans, having a growth mindset — recognizing that any failure or mistake is neither permanent nor a reflection of their own worth or ability, and by building their own resiliency to adverse circumstances and outcomes. It also helps to approach work with joy and gratitude.

7. Regarding funding, for women or leaders in general, the correlation isn't as clear, but whatever helps with developing good relationships along with strategy will go far in getting the needed funding.

Interestingly, when it comes to all of these, leaders already recognized many of the solutions themselves. That is, I only needed to add a few suggestions and/or highlight them here.

For any leaders reading this, which of these issues resonate with you the most? Which areas of competence and character speak to your situation and experience?

Isn't it reassuring to know you're not the only one? And isn't it more reassuring to know that solutions are not only out there, but in here when it comes to your own realizations and inner-development?

Go to eRep.com/core-values-index/ to learn more about the CVI or to take the Core Values Index assessment.

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Dr. Julie Tofilon

Dr. Julie Tofilon


Dr. Julie M. Tofilon, DMin., ACC, CPLC, is a Leadership and Career Coach with Springforth Coaching, BetterUp, PPCaDI, and Stone Allen Consulting. For over 35 years, including 15 years overseas, she has trained many people of diverse backgrounds, cultures, and ages in personal and leadership development, along with interpersonal and cross-cultural relationship skills. She currently helps visionary leaders become the kind of person others WANT to follow.

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