Last updated: December 14

Leading the soft (introverted) CEO 

Driving peak performance for CEOs and their boards, Westgate Executive Branding Offers Premier Advisory Services & Personal Branding Consulting for High-Profile Leaders. About Maureen—CEO & Founder. 

Working with a quiet CEO can be challenging because they often hold their cards close to their chest. The team often wonders how they feel or what they’re thinking. Why? Quiet CEOs are reflective and like to process information before responding. Give them space to reflect and then respond.

Avoid costly terminations and enhance the performance of introverted CEOs by learning how to approach the board with confidence or how to approach your operating partner with a key issue. CEO turnover and its cost to investors, reputational damage to the brand, and friction with employees are all risks associated with poor communication.

A study featured by SHRM reported that larger companies are at risk of losing an average of $62.4 million per year because of inadequate communication, while smaller organizations are at risk of losing $420,000 annually. Additionally, CMSWire reports that 97% of employees believe communication impacts their task efficacy daily. Finally, according to the Achievers’ report, 52% of employees say they stay in a job because they feel valued and supported. Learning how to communicate with the different leadership styles is crucial to the success of an organization.

In addition to this tool supporting team building and behavioral analysis, it also supports our proven system (C-Suite Optimization Program) that puts key messaging and authentic personal branding into the hands of the executive. The personal brand is a tool and corporate asset to help the CEO navigate the tricky and sometimes sticky relationships in the corner office.

Executive personal branding helps to uncover authentic messaging based on personal values using verifiable tools. Personal branding strengthens communications with internal and external audiences in a way that supports the corporation’s brand and its business goals.

This article is an extension of a very popular one we wrote discussing how to work with teams. This is the third article of 4 that we will be publishing over the next 2 months on the four primary leadership styles.

You might be interested in viewing the first two we published—the “type A” leader and the extroverted leader.

Executive performance optimization

At a recent business meeting in New York City, a private-equity executive (after listening to my value proposition) asked me: “Maureen, how do I get someone like you into my portfolio company? I know they need you, but how do we bring you into the company without accusing the CEO (or the board) of incompetence?”

It’s a great question, which we address in this article.

When to bring Westgate into your organization

Typically, we’re invited into organizations when:

There is a newly appointed CEO

  • To protect the board’s investment in the new CEO
  • To assist with an effective CEO transition with the new leadership team
  • To align internal and external messaging designed to improve CEO/Board engagement

When change is coming

  • Handing over the reins to a new leader
  • An IPO or strategic sale is on the horizon
  • Require a plan for the business post-bankruptcy

When change is overdue

  • Optimize the digital footprint for the CEO and leadership team
  • Raise thought leadership and visibility in the capital markets
  • Align the CEO and the board’s priorities

Organizations are led by various types of leaders: high drivers, extroverts, introverts, and analytical leaders. This article focuses on how to interact with and influence the softer, steadier CEO, Board Chair, shareholder or investor.

How to work with the soft and steady CEO

These executives value relationships. They value trust and authenticity. When working with these executives, talk in terms of feelings, not facts. They don’t want to ruffle feathers; they want to be assured that everyone will approve of them and their decisions. Give them time to solicit co-workers’ opinions. Never back this kind of executive into a corner—it is far more effective to apply warmth and sincerity to build a relationship with the steady executive.

The ideal work environment for this type of executive includes:

  • Sufficient time to adjust to changes in the workplace
  • Established practices, procedures, and protocols
  • Clear areas of responsibility with minimal ambiguities
  • Minimal sudden changes and crises
  • Sincere interest for the people in the workplace
  • A democratic direct report
  • The ability to interact with people in a comfortable, non-hectic manner

When leading a soft and steady CEO, Board Chair, shareholder or investor, understand the business and situation from their perspective. Softer leaders tend to be indirect, open, and empathic.

How do you know the person you’re dealing with (CEO, board chair, etc.) is soft and steady?

  • Tend to be very service-oriented, even as a leader
  • Willing to jump into a project, including day-to-day minutia without complaint
  • Tend to avoid controversy and hostility
  • Have a calming presence and can make others feel calmer
  • Persuade others by offering empathy, understanding, and friendship
  • Inclusive—feels comfortable when everyone else feels comfortable

The following infographic demonstrates their outward preferences and behaviors:

How to handle conflict with a soft and steady CEO (real or perceived) …

These executives can often feel as though their feelings, needs, and desires are not as important as those of others, which can encourage others to take advantage of them. This can result in repressed anger. That anger may build up over time and eventually (often over something trivial) lead to a trigger event, resulting in an explosion, releasing a torrent of angry words and litany of past offenses (often in considerable detail). Upon venting this built up emotion, they generally return to their normal behavior.

Remember, these executives seldom express their own feelings of anger or dissatisfaction, fearing that doing so might damage relationships and destabilize the situation. They tend to go along with what others want in order to avoid any controversy.

When working with these executives, clarify any instructions or communications they might not fully understand. Check in on them and make sure they know you support them (especially in approaching any significant change).

When presenting your ideas and opinions to this kind of executive, do so in a non-threatening way. Break the ice with a brief personal comment and plan some extra time in your schedule for talking, relating, and socializing with this executive.

When in doubt, ask for their input and provide assurances regarding decisions.

How to help the soft and steady CEO decide…

Deal with only one subject or situation at a time, one step at a time. Before moving on to other items, be sure they are ready, willing, and able. Remember, if they’re overwhelmed or don’t feel good about something, they may keep it to themselves.

Maintain a calm and relaxed demeanor. Encourage them to share their suggestions on how the decision might be made in a way that will add even more stability to the conditions.

“Would you mind writing down a schedule of your office’s activities so I can write my proposal without missing anything?”

How to encourage the soft and steady CEO…

Remember, these executives are relationship-oriented and thrive on trust, warmth, and authentic relationships. In building that trust, show them how their work benefits others. Connect their individual work to the benefit of the whole team and get them to see how their follow through links to a greater good. Ideally, use pleasant and patient approaches in smaller group settings.

Feel free to talk about things that support their dreams and goals. Offer engagement and input on how to make their ideas become a reality. You want to demonstrate your interest in them.

Stay organized and move steadily with them as you check to make sure they understand and accept what is being said.

“How do you feel about my staying in the office at a particular time each day in case you need to telephone me for emergency questions on this account? Are you comfortable with my calling you?”

How to compliment the soft and steady CEO…

Show them how they are effective in strengthening relationships with others. This will both compliment and encourage this type of executive. Mention their teamwork and dependability. Due to their relationship-oriented nature, how others regard them is very important. Remark on how well they get along with their co-workers and how important their relationship-building efforts have been to the company.

However, don’t go overboard. Gushing flattery can arouse their suspicions, so stick to praising attributes.

Know the fears of the soft and steady CEO… 

Understanding their fears is key to helping soft and steady executives succeed in their leadership roles. The challenge is that they will seldom tell you their fears directly. You must ask them and give them time and opportunity to answer the question: “Malcolm, it seems as though there is something on your mind.” Then stop talking and give them a chance to respond.

Generally, they fear change and instability. Reduce their fears by showing how specific changes will benefit them and others.

“Malcolm, moving will be an adjustment for all of us; about 80% of our staff has agreed to go. The company will move you and your family, sell your house, and give you a 10% bonus for your loyal service.”

Additionally, they don’t feel comfortable with the limelight on them, so be prepared to do more talking than listening.

How you can introduce us to your firm’s leadership:

Launch your offsite meeting confidently with our premier inclusion event.

Create inclusion and trust for your executive management team. Let people know you care by learning their behavioral styles and understanding their personal preferences for engaging with others.

This private event delivers a high return on time invested because you will walk away with a tool that takes the mystery out of people, making your relationships with your team members more meaningful, trusting, and effective.

The Main Event begins with a 1:1 conversation with the CEO and their team, followed by a group debrief that lasts approximately 40 minutes. It’s fun, safe, and provides strategies your CEO and team can begin using immediately.

For more information, contact: Maddison Shears at maddison@westgatecareercoaching.com.

Instant download below (Main Event Brochure)

Westgate's senior leadership retreat program

Maureen Farmer, CEO/Founder, is a Certified Personal Branding Strategist. She helps CEOs build authority, trust and elevate their credibility with capital markets, shareholders, investors, employees, and clients.


About executive resume writing author 

Westgate - Maureen Farmer

Maureen Farmer is the Founder & CEO of Westgate Executive Branding & Career Consulting Inc., an international personal branding and career consulting firm delivering premier executive branding and career consulting services for high-profile leaders. Author of The CEO Script Vault: Job Search Scripts for Busy Executives, Maureen believes that when we’re doing work aligned with our values, everyone wins. Using the law of attraction to identify quality employers utilizing the hidden job market is a cornerstone of her career management strategy.

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