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  • Writer: Matt Heelan
    Matt Heelan
  • Dec 26, 2022
  • 2 min read

Updated: May 22, 2023


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The Summary: I am writing this blog in an effort to share my insights, experience, and expertise from a 20-year career spent working mainly in technology with small to medium-sized organizations. Background: When I began my career in 1995, I was quickly promoted to become a manager of other human beings. I was not promoted because of my natural leadership and management skills. I was promoted because the organization was experiencing explosive growth and the CEO needed people to help manage that growth. I was young and eager so I said yes to the opportunity.


Unfortunately, there wasn't anyone to teach, mentor, or coach me on how to be successful in this role. As is typical in most small businesses you have to just make it up as you go along. I decided that I would take the initiative and just teach myself how to be a manager. I began by reading everything that I could find about management and leadership on the weekends. The following week I would take what I had learned and apply it in the real world. It didn’t go well at first.

Over the course of the next 20 years through trial and error, I began to improve and get better at leading organizations and managing people while I continued to be a “student of the game.” This brings us back to why I feel compelled to want to share what I know.


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The Bottom Line: 1. I know that there are individuals out there who want a resource where they can get advice about how to be successful in their new role. 2. I know that there are organizations out there that want to grow the company but don’t know how to do that. 3. I know that there are leaders and managers struggling with different approaches to building, motivating, and creating a culture of high performance. For all of these cohorts, I want this to be just one of the many resources you utilize in the vast array of tools that you need to be successful. It is my hope you might come here to learn from me, engage with me, and teach me. I intend to publish new content here weekly and covering topics such as:

  • Entrepreneurship

  • Planning

  • Strategies

  • Systems thinking

  • Design thinking

  • Agile thinking

  • Mentoring/Coaching

  • Confidence

  • Bullying

  • Scaling the business

  • Innovation and Transformation

  • Toxic culture

The Ask: Your time is precious therefore I appreciate any time you spend engaging with me about the content that is here. I would simply ask that you engage with me by:

  1. Hit that “Subscribe” button in order to receive the email which will notify you when there is new content.

  2. Hit that “Login” button in the upper right in order to become a member. Additional membership benefits will be coming.

  3. If you enjoy and receive value from the content please like, comment, and share. Conversely, if you don’t like the content also feel free to share because remember I am still a “student of the game.”

 
 
 
  • Writer: Matt Heelan
    Matt Heelan
  • Dec 1, 2022
  • 3 min read

Updated: May 22, 2023


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I understand there has been a lot written about the “Great Resignation” however several years ago I decided that I would use every November/December to reflect on my level of satisfaction in my role with the company. I don’t use any tools in order to make this evaluation but just put some serious thought around the following questions or topics: (1) Value of my time. Do you find the work that you are doing challenging and engaging? Do you find the work you are doing rewarding?

(2) Check your values. Do your personal values still align closely with the company values? And vice versa. (3) Check the culture. Organizations are living, breathing things and therefore so is the culture. Has the culture changed or evolved? Does it still align with the culture that originally attracted you to the company? Has the culture become toxic in terms of its willingness or desire to solve issues or problems? (4) Work/Life Balance. Does the organization make it easier or harder for you to achieve some sense of balance?

(5) Rewards. Have you achieved the goals that were set? If so, are you being properly rewarded for your performance and the organizational results? (6) Benefits. Have the company's benefits both traditional and non-traditional changed and improved? (7) Reputation. Is the organization that you are working for still viewed as a leader, innovator, or creative in the marketplace? Are they continuing to create value or have they become complacent?

(8) Learning and growing. Two somewhat different perspectives on this topic. Has the broader organization learned from its mistakes with respect to people, processes, and performance? Do you feel as an employee that during the past year you have grown in your own knowledge, skills, and experience? (9) Leadership/Management and Transparency. Do you know how well (or not) the company is doing? Do you have confidence in the team that is leading the organization? Have they made good decisions to achieve the goals of the organization? Have they connected you to those goals clearly? (10) Team members. The people you come to work with each day matter greatly. Has the organization done a good job of finding new team members that fit well within the team? Has the organization done a good job of working with those team members whose performance is poor? Have they acted quickly when it was obvious the team member was impacting the overall team's performance?


Lastly, and maybe more importantly, while you can choose to do this sort of self-evaluation it is non-negotiable that on a frequent basis the organization must solicit your feedback on how satisfied you are in your position/role. Of equal importance is what they do with this data once it is provided to the organization because sadly a fair amount of organizations fail to act on this feedback.


All of these questions and topics are all interconnected and our level of satisfaction for each moves along the continuum between dissatisfied to very satisfied. However, it is critical that you spend some part of your time reflecting and determining how satisfied you are in your position or role. I remind myself that life is short, and working with people who I like and respect is ideal, working with an organization that is respected for the work they do for their clients/customers and is financially rewarding is what we are all in search of.


 
 
 

Updated: May 22, 2023

I was talking to a friend of mine whom we will call Sarah. Sarah has been the CEO of a technology company for the last 10 years. She had reached out to me and said, “Matt, we are struggling to hit our financial goals each quarter. I know that we have struggled on the delivery side but I don’t fully grasp why. Can you help me figure this out?”

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The company that she was running was relatively small (60 employees), had been around for 10 years, and had a solid list of clients who consistently gave them projects. In addition, on the new sales front, her team was led by another woman, Julie, who had built an amazing team that was consistently exceeding their goals. We began working together to investigate the issue on the delivery side. We sat down with the COO, Jeremy, and tried to get his thoughts on the delivery issue. Jeremy cited some scope issues with a particular client, increased expenses, and challenges around productivity with people working remotely. He had a team of 3 Team Leads with each Team Lead having between 10-12 Team Members. These Team Members were project managers, analysts, developers, and engineers. The majority of the Team Leads and Team Members had been with the company for 3-5 years.


Sarah informed me that they were utilizing EOS (Entrepreneurial Operating System) for the past year and she really enjoyed the framework and the ability to focus on data, processes, and people. She had utilized some frameworks in the past but found them to be impractical and burdensome to implement. I had also been sharing with her over the course of our coaching sessions some tools and frameworks around Systems Thinking.


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As we started to dig into the data reported via each team's scorecards we noticed one team's results were all over the place in terms of the achievement of their goals. This team was run by Mike. I met Mike at the company’s planning meeting last year and found him to be a little “rough around the edges” in terms of how he interacted with his team members. Some of his teammates even described him as a manager as “somewhat disrespectful” “backstabber” and “hostile” in some previous employee surveys. Jeremy was working with him on improving his performance but in the meantime, there was significant attrition on Mike’s team.


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After several more conversations with Sarah, Jeremy, Mike, and his teammates we reached the following conclusions:


1) The poor performance and leadership of Jeremy and Mike were impacting the financial results of the organization. The simple fact was that no one wanted to work with Mike and because of this Mike became ineffective as a leader and his ability to get results out of his team members.


2) Jeremy worked too slowly to address the issues with Mike and was viewed by Mike’s team as being complicit in allowing his behavior to continue.


3) In a conversation with the Director of People Operations, Kristen, she noted that there were several notes made about Mike’s leadership style from her team's exit interviews with Mike’s outgoing team members. These notes were shared with both Jeremy and Mike.


4) Kristen also mention that Mike was promoted because he was considered one of the brightest developers and did some amazing technical work when he was hired 5 years ago. Because of his high level of performance as a developer, he was promoted to Team Lead by Jeremy.


5) Sarah noted the failure of this issue to get surfaced within their monthly EOS sessions as a Leadership team was baffling to her. Sarah also noted that she felt the organization failed Mike by promoting him to a role that was not a good fit and without a lot of support to improve his performance.


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In my experience, people feel the solution to eliminating a toxic work environment is to get rid of the root cause - the person or people contributing to the toxic culture. Systems thinking teaches us that we can’t just look at one component within the broader system but that we have to look across the organization.

Here are some systems-wide organizational questions:

1) How did we encourage and endorse this behavior?


2) Have the values of the organization changed such that somehow we are now promoting this behavior?


3) What systems and structures failed to alert us of the toxic behavior? Or if they were working why didn’t we listen?


4) What systems and structures do we need to improve in order to prevent toxic behavior in the future?


5) Why did our communication break down within the Leadership Team?


6) What is the overall cost to the organization for our inability to effectively deal with this issue?


I gave Sarah the following advice:

  • Focus on the organization as a system.

  • Utilize EOS and the principles around being clear about the vision, reviewing and analyzing the data, building and maintaining processes, getting and keeping the right people, and resolving issues quickly.

  • Find additional tools, frameworks, and systems and empower your team to utilize these throughout the organization.





 
 
 
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