Welcome to the Secret Sauce, a series by the Crystal team where we have deep-dive conversations with fast-rising sales leaders to learn about the most unique, potent ingredient to their success.
We asked Jaimie about her “secret sauce,” and her answer was simple: promoting from within.
Throughout her career, Jaimie has built out programs to support emerging leaders on their management journey. At Zendesk, she created a six-month “Rising Stars Program,” where people took active roles trying out managerial duties and activities to learn whether it was something they truly wanted to do. Those who then decided to pursue real management opportunities were more prepared and empowered to take on those roles.
As someone promoted to a management position early on herself, she knows how difficult the transition can be. Helping others make the leadership leap has become a professional passion for her:
“I’ve built my entire career from promoting within– identifying the people who are ‘we and us’ versus ‘me and I,’ who is building proactive best practices and demonstrating teamwork and leadership early on, and helping to mentor those folks to become leaders.”
In her training workshops, Jaimie advocates the importance of a defined customer engagement process and different strategies to strengthen leadership. Her lessons come from extensive firsthand experience witnessing the successes and challenges that many first-time managers experience.
“I want there to be more, better leaders out there. I’ve seen way too many bad ones!”
For her workshops, Jaimie describes “The Wizard of Oz Problem” to remind managers that they are not only managing on skills and knowledge but on qualities as well.
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Knowledge |
Courage |
Heart |
Skill |
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Example: Missing the forecast. This sort of information is knowledge a manager must have. |
Example: Not wanting people to hate them. Sometimes it may be challenging to keep everyone happy when making decisions, but it’s part of the job. |
Example: Being hesitant to let go of high-performing but toxic people. Have the gut and heart to recognize what is damaging your team and to act on it. |
Example: Needing a body to fill the quota. You want to have the right team in place and be able to empower them instead of waiting for others to do so. |
One of the other main pitfalls that many leaders fall victim to, Jaimie refers to as “going native”-- when leaders continue to think like individual contributors. This can be dangerous in three ways:
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Solo Operator Mindset |
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The Heat Shield |
The Rogue |
The Buddy |
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Managers are not doing what is right for the business because they don’t want to upset the team. |
Managers go rogue and try to run their own playbook when they disagree. This can lead to teams being disenfranchised from the group because they feel entitled not to follow the playbooks. |
Managers struggle with giving negative feedback that feels judgemental and may avoid having those important conversations altogether. |
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Instead: Look at things from a business perspective. |
Instead: Disagree, but still commit, move forward, and sell your team on why you’re moving in that direction. |
Instead: Frame negative feedback as a way to improve their perception and facilitate their growth as a rising star. |
The pipeline from individual contributor to manager often lacks roadmaps to ensure strong leadership. To combat this, Jaimie incorporates the book First, Break All The Rules in her workshops as a practical way to measure the active engagement of a team while holding managers accountable for being the leader that people want to work hard for. She highlights the importance of “The Measuring Stick” and “The Four Keys” as outlined in First, Break All The Rules. Both offer innovative ways to measure engagement and different approaches to contradict common rules in leadership.
Here are “The Four Keys” to being a great manager by breaking the conventional rules:
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Conventional Wisdom |
Different Approach |
Insights |
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Hire people based on experience, intelligence, and determination. |
Select someone based on talent. |
Rather than hiring based on experience and intelligence, make selections based on actual talent. You can’t teach talent, and most often talent is a driving force of performance. This is perhaps the most important responsibility of a manager– if they don’t select people for talent, then all the effort put towards growing them will be wasted. |
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Set expectations by defining the correct steps. |
Define the right outcomes, not the right steps. |
This allows people to have autonomy. By telling them what they need to produce, rather than what they need to do in order to do so, they can lean into their strengths to produce those outcomes. Each employee will have different motivations, needs, and ways of doing things. By celebrating diversity and encouraging employees to follow their path of least resistance when producing outcomes, managers can nurture responsibility, self-reliance, and self-awareness amongst their team. |
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Focus on identifying and fixing weaknesses. |
Focus on strengths rather than weaknesses. |
Instead of trying to fix weaknesses, learn how to manage around them. By focusing on strengths and cultivating each person’s unique talents, managers allow them to become more of who they are already. In embracing the unique talents of employees, managers can help them perform to their very fullest. |
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Develop people by helping them learn and get promoted. |
Help them find the right fit, not the next rung on the ladder. |
Managers should try to help employees find roles that highlight their unique strengths or talents and do more of what they naturally excel at. This will look different for each person. Rising stars want to progress their careers in some direction, while rockstars love what they do and want to continue doing well at what they’re doing. Both are equally important, and teams must have a balance of the two. |
Jaimie’s passion for nurturing emerging leaders is what drives her own personal leadership style. These are only a small handful of her insights after years of hiring, promoting, and training high-performers to become managers; for executives who want to dive deeper, she recommends books like First, Break All the Rules, Question Based Selling, and Fanatical Prospecting.
“Be the leader people want to work hard for.”