As the year comes to a close, sales leaders like myself are thinking about how we can set our people up to win in 2023. We’re running through technical checklists and asking ourselves: 

  • What number do we want to hit?  
  • How can we remove rep roadblocks? 
  • What programs can we optimize? 
  • Have we scheduled SKO? 

These are important questions, but we often get tied up in the technical aspects of leading a team and forget to take a closer look at who’s leading the team: us. The question many of us fail to ask is perhaps the most important:

What does my sales culture say about me? 

I recently led a guided self-assessment with John Dougan, Senior Director of Global Sales Performance at Workday, and Casey J. Ashley, Enterprise Sales Development Manager at Twilio Segment, to help sales leaders evaluate their coaching influence and effectiveness. The resounding thread throughout our conversation was this: How we show up as leaders has a material impact on our team’s performance. From energy to efficiency to goal attainment, each team is a reflection of the person who leads it. 

What standard are you setting for your team, and is it working? In this blog, I’ll break down 4 powerful qualities of successful sales teams and how we as leaders, coaches, and managers can transform coaching from isolated programs into cornerstones of culture.

1. Invite authenticity

Authenticity isn’t about putting all your thoughts, feelings, and opinions on display—it’s about being genuine. Say you’re in a 1:1 coaching session and ask a rep how their weekend was. Do you actually mean it, or are you simply checking a box? Your rep will know the difference, and that will affect how they communicate with you in the future. 

Strong relationships are built on trust. When you show up authentically, trust happens naturally, and your people will feel safe to do the same. They’ll be more honest about questions, challenges, and feedback. That’s where collaboration, coaching, and growth will thrive. Not to mention, your people will bring their whole selves to work and contribute amazing things to your culture. 

Ask yourself: 

  • Am I aware of how I come across to others? 
  • Am I cognizant of how I communicate with people on my team? 

Expert insight: “I’m going to be more authentically myself, more aware of how I come across in different scenarios, and make a conscious effort to truly understand and know my audience.” – Casey J. Ashley

2. Act through awareness

It’s easy to make swift decisions from a place of emotion, desperation, or urgency, but our response will be less effective if we don’t first assess the situation from all angles. To make a lasting impact from a coaching perspective, we must be thoughtful and strategic rather than impulsive. We have to understand where our reps are, where we want them to go, and then decide what we’re going to do to help them achieve that goal. 

Every coaching conversation must start with awareness. As leaders, we must be aware of ourselves and how we can best communicate with and motivate each individual on our team. Acting through awareness means considering your people and goals in place before plotting the path forward. 

Ask yourself: 

  • What is the “why” behind my decision or approach? 
  • Is this really the best path forward for me and my people? 

Expert insight: “If you can create a pause between the stimulus and your reaction, I would consider you a fairly developed leader.” – John Dougan

3. Lean into team strengths

Different teams have different personalities. Some are high-energy and some are quieter, but both can be extremely effective. Part of your job as a leader is to establish your team’s identity. Without an awareness of the specific strengths each individual on your team brings to the table, you can’t create an authentic identity, and your team will be less effective as a result. 

Pay attention to where and how team members shine and delegate to them. Empower them with opportunities and additional responsibilities. If you have a rep who aspires to be a manager, let them lead a team meeting. When you lean into your team’s strengths, you’ll find countless real-time coaching opportunities and give people the opportunity to grow in the process. 

Ask yourself: 

  • What are my team’s strengths? 
  • How can I leverage those strengths and bring out the best in my people for the benefit of everyone? 

Expert insight: “Leaders—are you that person that people plug into to get a recharge, or are you draining their battery?” – Casey J. Ashley

4. Hold yourself accountable

At Ambition, we talk a lot about accountability. Outlining clear expectations and goals for your team keeps everyone aligned and on track to influence key business metrics. People who are aware of the areas in which they need to improve bring more discipline and resilience to their work, and they see performance gains as a result. 

This sentiment is true for everyone. Leaders who hold themselves accountable to constant growth and improvement are statistically proven to have more successful teams. 

Ask yourself: 

  • Am I aware of my strengths and weaknesses? 
  • Am I leading by example and actively investing in those areas of growth?

Expert insight: “We must hold ourselves accountable to a series of standards so that our people hold themselves accountable to their own standards that they have developed as a result of their relationship with you.” – John Dougan

Watch the Guided Self-Assessment 

During your end-of-year reflection and planning, ask yourself: How does my level of self-awareness impact my people, culture, and coaching influence? As Casey mentioned during our conversation, “Self-awareness is not always evident and can be developed over time.” Now’s the time to begin. Watch the on-demand webinar here for more tips, questions, and insights to help you develop more self-awareness and lead your team to greatness in 2023 and beyond.  

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