So Your Boss Is an ESTP Personality: 3 Strategies for Enjoying the Storm

Through their unique leadership style, ESTP bosses can create an environment that’s exciting yet potentially difficult to work in. By understanding their personality type, you can learn to maneuver the challenges that they bring to the workplace and propel your own professional growth.

Have you ever felt like you’re working in the midst of a hurricane, with your boss’s decisions flying at you from all directions and their priorities shifting around faster than you can blink? If so, your difficult boss might be an ESTP personality type (Entrepreneur).

ESTPs are dynamic individuals who bring a unique energy to leadership roles. They tend to create a work environment that’s both exhilarating and – let’s face it – sometimes overwhelming for personalities who don’t exactly operate with the same level of intensity as they do.

If you happen to be one of those personalities who struggle with the energetic and sometimes frenetic leadership style of an ESTP boss, don’t worry. With the right approach, you can not only learn to weather the daily storm but also come to appreciate – and, dare we say, enjoy – the variable working conditions.

If you’re not sure whether your boss is an ESTP, consider using our free Type Guesser tool for the workplace to make an educated guess about which personality type they might have.

Understanding Your ESTP Boss

Before we jump into practical strategies for dealing with your difficult boss, let’s take a closer look at the ESTP personality type. As Extraverted, Observant, Thinking, and Prospecting individuals, ESTP personalities can best be described as practical, outgoing, and action-oriented problem-solvers who thrive on variety and immediate results.

ESTP bosses typically have a leadership style that is defined by a unique, hands-on approach. They often prefer to lead by example rather than through rigid hierarchies. Quick decision-making, adaptability, and a focus on doable solutions are hallmarks of their personality. They’d rather roll up their sleeves and tackle a problem than spend hours in meetings discussing the situation.

Working for an ESTP is rarely boring, and even the most mundane task can become downright exciting under their leadership. These bosses often excel in crisis management and are generally open to new ideas. They also have a knack for spotting opportunities, which often results in the chance for those who work under them to tackle some interesting projects.

All that sounds great, but if you work with an ESTP leader, you know that these personalities also have their fair share of blind spots that can make their leadership style difficult to deal with.

ESTPs are prone to prioritizing short-term gains over long-term planning, and this can lead to a lack of strategic direction. Their quick decision-making can sometimes come across as impulsive, and they might struggle with routine tasks or detailed paperwork. ESTPs are also known to sometimes overlook the emotional aspects of leading a team, which could possibly cause some team members to feel ignored or snubbed in the high-energy working environment that ESTP bosses tend to create.

To learn more about difficult bosses and personality, be sure to read our article “‘My Boss Hates Me!’: Personality and Difficult Leadership Styles.”

3 Strategies for Navigating the ESTP Leadership Style

Now that we’ve got a handle on what makes your ESTP boss tick, let’s talk strategy. How can you deal with your difficult boss? Well, it all boils down to finding ways to adapt your work style to resonate with their personality – all while staying true to yourself.

Strategy #1: Practice Precise Communication

When dealing with your ESTP boss, remember that these personalities appreciate directness. Consider the following advice when discussing work projects with them:

Be concise and to the point.
Focus on facts and immediate implications.
Be ready for rapid-fire exchanges.
Use visual aids when possible.

This direct and rapid communication style might feel uncomfortable for some personality types. For instance, Introverted personalities might prefer more time to process information, while those with the Intuitive trait might struggle to concisely communicate the practical implications of their key points.

If you sometimes struggle to communicate with your ESTP boss, consider preparing talking points for project discussions in advance. For unexpected questions, have a ready response that will buy you time, such as “Can you give me a minute to double-check my facts and let me get back to you on that?”

This approach allows you to adapt to your boss’s style while ensuring that you communicate what you need to say effectively. With practice, you’ll find a middle ground between their preferred directness and your natural communication style.

Strategy #2: Focus on the Present

Even more important than how you communicate with your ESTP boss is what you communicate. When reporting to them, it helps to stay focused on what is happening in the here and now. To accomplish this, you can try the following tactics:

Highlight the tangible results and immediate benefits of your work.
Describe long-term projects using anticipated milestones.
Provide fact-based updates.
Never present a problem without also presenting a possible solution.

Intuitive or Feeling personalities may be tempted to present emotional insights or intangible concerns as data points. To overcome this temptation, consider how you’re framing the information that you need to communicate. Be intentional about which information you share, what you emphasize, and how you present it. This helps shape your message in a way that your boss is most likely to hear.

Despite sharing the same trait with their boss, some Prospecting personalities – particularly those with the Intuitive trait – might struggle to break everything down into clear, viable steps or to quickly find solutions. These personalities can take heart in the fact that ESTP bosses are inherently flexible, so it’s usually okay if a proposed action plan or potential solution is not fully defined. Your boss is most likely looking for a starting point from which to tackle their problem.

For Judging personalities, on the other hand, the difficulty is likely to lie in finding the agility that’s needed to change course in a plan at a moment’s notice. This brings us to our next strategy.

Strategy #3: Embrace Flexibility

Embracing flexibility is crucial when working with an ESTP boss. Resisting the fluid nature of their leadership style will only lead to frustration. Instead, you can use the following methods to incorporate flexibility into every aspect of your work:

Always be ready to act quickly.
Present multiple options for dealing with issues.
Remain open-minded to unconventional approaches and new experiences.
Keep plans open-ended.

Learning flexibility is similar to learning to surf – it’s all about finding a balance between thorough analysis and quick action. For more methodical thinkers like Judging personalities, speeding up the decision-making process may feel risky and uncomfortable. This is only accentuated when plans are prone to changing unexpectedly.

If you struggle with this aspect of your ESTP boss’s leadership style, try to proactively anticipate changes and incorporate flexibility into your expectations. Remember, for ESTPs, “plans” are simply a series of options. The next steps that they choose to take will always depend on how things unfold.

Try to embrace this way of working and incorporate this mindset into how you perform your job. While it may never feel entirely natural, aligning your expectations with the reality of working for an ESTP can help you navigate their leadership style more effectively.

Maintaining Your Well-Being

Adapting to your ESTP boss’s leadership style will likely take you well outside of your comfort zone. Just remember, the goal isn’t to fundamentally change who you are but rather to develop a strategic approach that complements their style – while honoring your own strengths and needs. To do this, you need to carefully tend to your personal well-being.

This can be challenging in an ESTP-led environment, particularly for Feeling or Turbulent personalities. To stay grounded, you must recognize that your needs and emotions are valid concerns, even as you learn how to deal with your difficult boss’s leadership style.

You must also understand that your well-being at work is primarily your personal responsibility. Unless your ESTP boss has intentionally worked to develop their emotional intelligence, they’re unlikely to proactively take interest in or accommodate your emotional needs.

In a practical sense, self-care in the workplace means clearly communicating your needs. This can be accomplished by saying no to tasks that are beyond your area of expertise or responsibility or by asking for the support and resources that you need to perform your job to your boss’s standards. You might also want to find strategies that allow you to incorporate moments to recharge into your workday, such as taking an out-of-office lunch break or a walk after work to decompress. And don’t forget to reach out for support when you need it. Share your frustrations with a trusted friend or seek professional guidance if needed.

Dealing with a difficult boss doesn’t require you to sacrifice your own personality for the sake of survival in the workplace. It’s just a matter of finding strategies that allow you to perform effectively in your role without ignoring your own needs. With patience and practice, you’ll be able to do exactly that.

Final Thoughts

Dealing with a difficult ESTP boss can be challenging. However, if you embrace the experience, it can also be an opportunity to develop valuable skills to help you handle diverse workplace dynamics in the future. With patience and practice, you’ll learn to stay the course whenever the workplace winds get chaotic. Sure, there will be moments of frustration, but there will also be moments when everything clicks.

And who knows? You might surprise yourself by not just surviving but thriving under your ESTP boss’s leadership.

We’d love to hear your experiences. If you’re an ESTP leader, what insights can you share about your management style? And if you work under an ESTP boss, how have you navigated this relationship? Share your stories in the comments below, and let’s learn from each other’s experiences!