What Sales Leadership Style is Required to Succeed?

Sales Leadership Style

BOLD Sales Leaders will perform best in a rapidly changing environment.


It is not the most competent or the smartest sales leader that will survive, but rather the sales leader that is BOLD and can adapt to change will thrive.

There is no denying that you, your people, customers, suppliers, and stakeholders are dealing with unprecedented change.

Inflation, supply chain issues, the great resignation, competing demands, information overload and resulting overwhelm have consumed most sales leaders.

I don’t care if you are the head of sales or a front-line sales manager. It is incumbent on you to adapt to the change and lead your team to succeed.

The challenge you face is twofold. Senior management is risk-averse and not supportive of change initiatives, and your people are resistant to more change.

So, what are you to do?

The status quo will not achieve the results you desire or need.

You can put your head in the sand and hope for the best, or you can step up and be a BOLD leader.

Now is not the time for timid leadership. It is time to step up and be BOLD and take decisive action.

The choice is yours.

Three characteristics of a BOLD sales leadership style

I have worked to help my clients become BOLD sales leaders in the face of crisis. These are three areas that I have coached them on:

  1. Develop new strategies and find ways to get them implemented and executed
  2. Fight to get their salespeople what they need to succeed
  3. Being comfortable with having BOLD conversations

BOLD Conversations

I can’t tell you how many conversations I have had with clients on how to address a specific rep issue. I am sure you have at least one sales rep that is not performing up to expectations and need a BOLD conversation.

Issues such as:

  • Poor sales performance
  • Lack of activity
  • Minimal progress in skill development
  • Behavioral
  • Appearance or personal hygiene concerns
  • Compliance issues

Whenever I coach clients on BOLD conversations, they are pleased with the outcome. One of the benefits of having a sales leadership coach is having someone help you work through and prepare for a difficult/bold conversation.

Every issue is different, and how to handle bold conversations can be broken down into steps.

5 Steps to Conducting BOLD Conversations:

1. Prepare for the Conversation: There is a direct correlation between how well prepared you are and how well the meeting goes. Identify the issue, note your observations and feedback, generate reports, and develop a list of questions.

2. Seek to Understand: Ask a series of questions to determine if the rep is aware of the issue(s). If not, present the issue.

3. Gain agreement: On the issue and knowledge that feedback is clear.

4. Develop a POA: Have the salesperson develop a plan of action for the problem, the steps to address it, and timelines. Have them send you a copy.

5. Follow Up: Set several times for follow-up on the plan of action.



To succeed in today’s rapidly changing environment, a BOLD sales leadership style is best. Approaching difficult conversations head-on is critical for your success. Having a sounding board to prepare for a performance discussion can make all the difference in the outcome. If you don’t have a coach or mentor, follow my five steps on how to conduct BOLD conversations.

Are you a top sales leader? Take the Sales Leadership Self-Assessment and see how you stack up. If you want to discuss your results, I would be happy to book a 15-minute laser-focused review call.



Steven Rosen - Book a Call
Steven Rosen - Book a Call

Seeking BOLD SALES LEADERS looking to build a winning team and develop a performance culture that achieves outstanding results.

Are you ready to consistently exceed your sales objectives by 10-20%?

Steven Rosen 2022

Hi, I’m Steven Rosen, and I’ve been coaching sales executives for over 20 years!


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Steven Rosen - Executive Sales Coach


Steven A. Rosen

Steven helps companies transform sales managers into great sales leaders. His focused coaching helps clients achieve greater personal and professional success. Steven is the author of 52 Sales Management Tips - The Sales Manager’s Success Guide.

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