Every Leader Has Flaws. Don’t Let Yours Derail Your Strategy.

That strategy execution is one of the greatest organizational challenges is nothing new. The causes of derailed strategies have been well chronicled — from not actually being strategies, to organization dysfunction and misalignment, to excessive internal focus. But there’s (at least) one more stone to turn over in the hunt for answers, and it’s within the leader themselves. The effects of a leader’s personality on an organization’s culture have been long understood. But we believe that some personality flaws have a disproportionately negative impact on the quality and execution of strategic choices — in particular, where to focus, how to compete, and what to build (and discard). We find that just when leaders need to bring their “A game,” they get in their own way. It might be excitement or fear that reduces their ability to self-regulate their reactions. Instead of thinking clearly, they default to habits influenced by deeper and well-reinforced “personality flaws” — or in some cases, leadership pathologies. These are far more than just annoyances, as they cast a large shadow across their organizations, contributing to failures in the design and execution of strategy. Based on our combined 60 years of experience, we’ve identified four personality flaws of leaders and their specific impacts on strategy. For each type, we set out mitigating actions leaders can take.

The Overconfident, Chronically Certain Leader

An overconfident, chronically certain leader has a tendency to overpromise and develop unrealistic strategies. This creates unnecessary anxiety for the people charged with their execution. These leaders also suffer from myopia and over-determinism, oblivious to the impact of longer-term trends, complex dynamics, and disruption from new entrants. By the time they realize what’s happening, it’s often too late to respond. One of David’s clients, John, was the CEO of a midsize organization. He made bold, provocative statements about the future and didn’t listen to alternative views. Rather than motivating his team, he was close to alienating them. David suggested a first move that would enhance his awareness of his context without requiring him to make a dramatic change: Appoint a seasoned industry advisor he respected to mentor him. This created a safe space for John to reflect on the validity of the assumptions he had baked into his plans. If you lean toward excessive confidence in your views, here are some ways to mitigate chronic certainty:

• Orchestrate debate and dissent. Explicitly ask for different views at the beginning of sessions and say that it’s okay to disagree. Going one step farther, deploy separate teams — composed of people with different backgrounds, expertise, and styles — to “pitch” ideas against each other.
• Assemble people with the courage to challenge you. Guard against the temptation of working with “yes” people. Find people who are confident in their abilities and comfortable in their skin and encourage them to speak out when they disagree with you. Reassure them that their views will be heard and respected.
• Immerse yourself in external developments. Invest the time to identify weak signals, particularly about consumer behavior and technology innovation; observe competitor moves; and talk to key stakeholders to fully understand their interests.
• Invite outside voices. Retain advisors and former executives who have the experience and detachment to call out limiting or false assumptions and challenge unwise moves.

The Impulsive Leader

We’ve all seen the leader with “shiny object syndrome.” They can’t resist the titillation of a new idea or the latest fad. They crave the adrenaline rush of pioneering what’s not been done. In the process, they exhaust their organizations, overcommit resources, and overpromise to customers and shareholders. They tend to speak in flashy, hyperbolic declarations that whip people into frenzies of excitement. This soon dies down once they catch on to the pattern of abandoning last week’s big idea to pursue the next one. Instead, they wait it out, unable to sustain focus on something long enough to see it through. One of Ron’s clients, Eduardo, was division president of a global apparel company. He prided himself on his entrepreneurial success launching new products and influencing fashion trends. But his inability to restrain his impulsivity with the discipline needed to see strategies through proved costly. Warehouses became full of inventory rejected by retail buyers who’d started to lose faith in Eduardo’s brands. The more desperate he felt, the more impulsive he became. Ultimately, the best solution was to find a role more suitable to Eduardo’s creative strengths in another part of the company. If you struggle to resist the “next new thing,” here are some approaches to consider:

• Insert time and data into strategic decisions. Create gating factors in your process — things that force you to pause. In particular, require others to bring competing fact bases to the table and allow sufficient time in the strategic decision-making process for proper debate. This will help test your ideas before you act on them.
• Build extra discipline into the strategy process and allow others to run it. Like giving the car keys to a designated driver at a party, it’s important to recognize that while your instincts may generate lots of creative ideas, you aren’t the person best suited to own the strategy process. Surround yourself with disciplined leaders who can develop, interrogate, and pilot strategic opportunities in ways you would naturally avoid. This will allow your views to be tested in the open, building trust along the way.
• Over-index on risk factors and resource requirements. Be especially vigilant about the risks inherent in your ideas. Invest the time to identify the true scale of capabilities and resources required to execute them. Listen a bit more closely to the pessimists in order to understand risks fully.
• Get to the heart of your adrenaline binges. There’s something addictive about the rush of a new idea and the dopamine hangover that results. Dig into your motivations to find out what deeper need your bingeing might be meeting. In Eduardo’s case, we learned that his identity was so rooted in being a fashion pioneer that the notion of building on existing ideas made him feel inadequate.

The Rigidly Controlling Leader

Some leaders create a highly controlled environment. Everything — and everyone — works in a prescribed way. They struggle to accommodate novel or nontraditional views. This silences the voices of employees, who in turn produce low-risk, barely incremental strategies in order to avoid their leader’s exacting critique. They retreat from coming forward with creative ideas. When it comes time to execute, the fearful organization cowers from trying anything new, making change much slower, if not impossible. Sarah, one of David’s clients, had all the hallmarks of being a controlling leader. Meetings were orchestrated with precision, her diary managed tightly, and the people she interacted with carefully chosen. She found herself excluded from creative discussions, as others discounted her ability to explore beyond her purview. Maintaining this level of control was exhausting for her (and everyone who supported her) and took its toll on her health. Returning to work after a long illness, she found that her direct reports had performed well in her absence. This led her to reexamine where she could release control and explore better uses of her time. You can mitigate your tendency to over-control by learning to:

• Increase transparency. Share more information and insight about the performance of the business and the progress of activities. This engenders trust, and with time participation from others, which can reduce feelings of uncertainty and fear of other’s motives.
• Take calculated risks. Identify situations that are not sensitive or material to experiment with new ways of sharing responsibility and empowering others.
• Test ideas with trusted colleagues. Learn to communicate your thinking and ideas with people you respect. Open this circle to others as you find that this dialogue both improves the quality of ideas and increases buy-in.
• Examine your aversion to curiosity. Take the time to reflect on episodes in your career — and life — that may explain your controlling behavior. Were you mirroring the style of your boss? Was control your response to feeling like an imposter? When you showed some curiosity, were you castigated? Ask yourself how much this experience hinders you from performing at your best. And, most of all, work out what you want to leave behind.

The Insecure Leader

While every leader faces a crisis of confidence at some point, some leaders live with a paralyzing sense of self-doubt. They worry about what others think of them and anxiously expect to fall short. Many find ways of masking these deeper feelings with a confident game face and measured demeanor. Some are overly accommodating and nice. By purchasing the regard of others with benevolence, they reduce their deeper fears of failure and rejection. These leaders have a particularly noxious effect on strategy. They’re often taken advantage of by more aggressive leaders who cajole them into saying yes to every idea they’re offered. In addition, many are so fearful of failure that they end up with “a nalysis paralysis” and endless mitigation efforts for risks only they can see. They often refer to past failures as the basis of their risk concerns, no matter how long ago they took place or how much has been learned since. Linda, a former client of Ron’s, is a case in point. She was the chief marketing officer of a growing clean energy company, hired to reposition the company’s brand to serve a variety of new markets. Her background prepared her well for the role, but her anxiety about failure eroded others’ confidence. The CEO expected her to show up with well-formed ideas and recommendations, but she kept coming in with “rough drafts” under the guise of engaging the team to enlist their ownership. They interpreted it for what it really was: an insatiable need for approval and affirmation. Her insecurities led to numerous market launch delays and unclear brand messaging. Fortunately, Ron was able to help her get to the root of her fears and pivot, regaining some lost ground. If you suffer from an anxious sense of self-doubt, here are some ways to reduce their impact on strategy:

• Get to the heart of your fears. Whether with the help of a coach or therapist, recognize that pervasive insecurity is a sign of deeper unresolved issues. Linda was able to name the origins of her need for others’ approval and gained a more objective sense of her own abilities as a result.
• Do worst-case and best-case scenarios. Rather than catastrophizing over impending failure, insecure leaders should employ the use of reliable data to build realistic scenarios about the numerous potential outcomes of a strategy under consideration.
• Reframe the conversation to opportunities. Rather than remaining fixated on what might go wrong or how others might see you in a negative light, force yourself to look at the upside of opportunities you’re exploring. What’s the best possible outcome? How could the organization benefit? How might this put you in a positive light?
• Relive past successes. Sometimes the best way to contradict hypervigilant insecurity is to look honestly at your past successes. Where have you faced similar choices that turned out well? What lessons from that experience could apply now? Invite a trusted third party to give you a dispassionate view of your past, too.

All leaders arrive with some blemishes on their personalities. Those parts of our humanity can be a great source of vulnerability and connection to those we lead. But when those blemishes extend too far, they can be particularly destructive to the visions we’re casting and the strategies we’re executing. For some, the question isn’t “Which are you?”, but “Which are you when?” You already face plenty of obstacles to bringing those aspirations to life in the competitive landscape and within your company. Be sure that one of those obstacles isn’t you.