Talent Management in Action: One People Manager's 3-Pronged Approach to Fully Developing His Team

I would define my people management style as part Michael Scott and part therapist. Like Michael Scott from “The Office,” I am quite candid by nature and tend to lead with personality. And unlike Michael Scott, I have a pretty specific communication plan for my team. One of the lessons I learned early on was the best way to keep people on the same page is to make sure everyone has access to the same book. That said, being open and forthright has become a big part of my managerial style.

The purpose of this post is to discuss my management style as it has evolved and share lessons I have learned through both challenges and successes. Right now I manage the Sales Operations team at Greenhouse which is comprised of several highly skilled positions including Operations Manager, Sales Engineer, Productivity Manager, and Salesforce Administrator. In my previous roles, I have managed only sales people with quotas which posed its own specific challenges, but I find managing this diverse Sales Operations team more challenging and more rewarding. After all of the years I have been a people manager, I still somehow manage to learn something new every week.

Below I will share my unique 3-pronged approach to managing and empowering a successful team.

1. Vary the types of one-on-one meetings

An important part of managing people is to schedule time for one-on-one meetings. That time is great for getting to know your team as individual contributors. In order to be both productive and respectful of time, it requires structure and continuity. I prefer having a weekly one-on-one with each member of my team (between 30 minutes and an hour depending on the project load and the role).

Our current process is to have a tactical one-on-one followed by a strategic one-on-one. In the tactical sessions, we focus on projects, and in the strategic sessions, we focus on ideas and professional development. I like to think of the tactical meetings as “How tos” and the strategic meetings as “What ifs”.

In the tactical meetings, the team comes prepared with project lists, deadlines, and asks from leadership, keeping us productive and on task.

In the strategic meetings, we talk about creative ideas to reach company goals, individual career tracks, and focus more on long-term planning. In addition, we discuss professional development. This is the meeting where we talk through upcoming conferences and trainings that the team could attend. We also talk through career ladders and begin to map our projects that point each member of my team in the direction they want to go.

A recent example would be my Operations Manager’s track. Right now she has a deep focus on technology implementation, reporting, and documentation of processes. We started to discuss what her next role would be and came up with two avenues: the first would be more ownership over her current areas of expertise along with more direct reports in that area. The second would be to stretch into the training and sales engineering leadership areas which puts her directly in line for my role. Building out these tracks and assigning projects to stretch my team in that direction keeps them engaged and challenged.

The tactical/strategic approach has been successful as it has given me deep insight not only into the project load of my team but also into what drives them as individuals. I learn about their lives and personal challenges and feel free to share my own as well. Having a relationship built on trust and understanding creates a safe space for the more awkward conversations that are the less fun part of management. (More on that later).

2. Build a bulletproof team

A big part of my style as a people manager is focusing on what most refer to as “team building.” It’s not just about my one-on-one relationships with my team. It’s about the feeling of unity we have as a group. My job is to set the tone for this particular mentality. I use the phrase “bulletproof from the inside” because if we are united as a team, work well together, and have each other’s backs, we can remain both positive and productive in our work no matter the challenges around us.

One of the ways we established ourselves as a team is by having a quarterly breakfast offsite to spend quality time together. As a team we make it known consistently that we have each other’s backs. Although I am papa bear whose job it is to protect my team and face down any blockers to our initiatives, I still need their support, too, as I present initiatives and ideas to them and the rest of the sales organization. Each of us acts as an ambassador for our team, and we represent ourselves as a united group to the rest of the company.

Because the Sales Operations team administers the CRM and all of the other technology we use to assist the sales process, we sit directly in the line of fire. When there are bugs with new technology or a change in process challenges a sales team member’s adaptability, my team often bears the brunt of the challenges in a culture of change. Sales Ops is a demanding role that requires a lot of time and attention to detail. Everything we do as a team impacts everyone in the sales organization whether it’s something as complicated as a process change or as subtle as a new field added to Salesforce. Frequently, the buck stops with Sales Ops when it comes to any type of technical roadblock. There is something very humbling about being part of a team that actively protects each other and stands unified against any challenge.

3. Make time for #awkward conversations

Recently on a recommendation from one of the leaders on our People Team, I added an awkward conversation segment to my one-on-ones. This came about as I faced a new challenge in my managerial career. One of my company leaders sat me down to discuss an issue with how I was being perceived by my team. I was questioned about how/if I add value to my team and what my team thought about me as their leader. Each member of my team met with the leader and gave their feedback and then I met with each member of my team for direct feedback as well. At the end of the day, those conversations gave me an opportunity for growth and to expand my style to regularly include awkward conversations. To me an awkward conversation is any conversation that could feel awkward to either (or more often) both parties. It’s usually around a subject that could be more personal and often could be taken badly.

I solicit the awkward conversation by asking for candid and uncensored feedback. I feel like I create a pretty safe space for my team. Every challenging perception from my engagement as a leader to how I represent Sales Ops had been discussed at one point or another. I started off the initial conversation with the disclaimer that I can’t be a better manager until I know what I am doing right and wrong and I trust the people I work closest with to give me the most honest and critical feedback. That week I got all of the information I needed to confront challenges head on, but the real benefit was in developing a new level of candor with my team. Some of the feedback was challenging to hear, and of course, I wanted to immediately dispute all of it and give detailed explanations for any misinterpreted behavior. Instead, I held my tongue and took everything as constructive criticism and assigned myself an action item for every theme of the feedback.

The “awkward” part of the awkward conversations is far less awkward nowadays. I have no trouble asking questions about where I am lacking in expectation and reputation and my team has no trouble answering them. I have also learned the “caution” words each member of my team uses and what they mean. Caution words are words or phrases that are specific to each member of my team that are red flags for me and a reason to dig a little deeper into those conversations and keep an eye on the situations attached to those red flags. One member of my team uses “alarming” while another uses “concerning.” Understanding what these words mean to them in the context of the awkward conversation allows me to prioritize how I handle the challenging situations that come up.

Final thoughts

My best practices as a people manager include structuring meetings in a way that engages my team both tactically and strategically, building a “team” mentality, and making time for #awkward conversations to head off any challenging scenarios at the pass.

What I’ve learned the most in my role is that when people feel challenged, listened to, part of something they take pride in, and able to communicate freely, they are much more likely to be motivated to do the best work of their careers. And as a people manager, I couldn’t ask for anything more.


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Chad Dyar Headshot

For over 20 years Chad Dyar has been balancing his work in the ARTs as a performer and advocate with a communications-focused sales and sales operations career. The author of "How To Talk To Humans" has focused on building a deep and diverse network of connections. In 2015, Chad joined Greenhouse as Director of Sales Operations, where he has built out a unique and high impact ops team. Leveraging creativity, leadership, team building, and organization have helped him achieve visibility in the fields of sales/sales operations as a speaker, blogger, and super-connector. Recently, Chad started the NYC Sales Operations Meet-up bringing together sales and operations leaders from across the country to share best practices and experiential knowledge. Connect with Chad on Twitter and LinkedIn.

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