How an Unsexy Coaching Process Saved My Career, Part Two

Joseph Rupp
7 min readOct 15, 2020

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Joseph Rupp, Sugar High Motivation

Photo Courtesy of Jamie Street

I’m going to start the second post with an acknowledgement. My boss, who shall remain nameless only because he might not want to be named, was phenomenal. He supported my efforts and never hesitated to give me the freedom to do what I felt was needed. He provided guidance when necessary and a cover over many years. He was a tremendous leader and mentor: strategic, practical, driven and genuine. Interestingly, his one defining characteristic, beyond his prodigious dexterity with forecasts, remained his ability to stay calm in the face of incredible pressure. He held responsibility for the entire sales organization and over $1.7B in revenue and barely broke a sweat publicly. If sales were great, he was in a good mood. If sales were terrible, even and steady. I don’t know that he understands to this day how effectively that temperament served his entire organization.

I digress. I hired a consultant to help us build the platform (I use the term generously.) His name is Steve Johnson at Next Level Sales Consulting and author of multiple books including Selling is Everyone’s Business. Incredible energy and sales skills. The only thing I told him was that I needed to embed the organization with a coaching mindset and toolset. I need to state this as well. I had worked in multiple organizations where we focused heavily on genuine coaching. In fact, I once had a boss who went to great lengths to embed the behavior across her organization. So, I had experience cultivating it. But, in this instance I needed not only the behaviors, but a well-defined process. I got more than I expected.

I wanted to see our associates, sales managers, feel the benefit and the standard — you teach what you accept — of working in a truly supportive, demanding and disciplined organization. With Steve’s help, that is precisely what we built. And the changes happened almost immediately. I’ll walk you through the process.

The Form. I am convinced that anyone who has worked with me on this format will recoil at mention of the form. However, that form helped define the framework for the most important element: the results, the leading indicators and the conversation. We designed the process so that the associate would lead the conversation with occasional guidance from their manager. I wanted our team members to feel both ownership and leadership.

I will not go into the minutiae of the form. I’ll give you a broad outline and a few specifics. It was always about the process. It is always about the process. The form defines the steps. My own efforts to provide leadership to individuals and organizations in my current role relate in part to the success we had leveraging the process — although I have simplified it greatly in Sugar High Motivation. Back to the format.

The form established a discipline of thought. It created a monthly journey every associate followed at least once a month. The elements of the form will appear boiler plate to most people: tell me your greatest achievement last month | biggest challenges | how did you fare to your individualized territory plan. The purpose of the questions was very straightforward — start by eliciting a success story and establishing both a positive mindset based on a positive outcome and then review the follow up items. No surprises here.

The heart of the form focused on Key Performance Indicators. We did not plan to review the actual to plan revenue results in this conversation — it happened anyway — but the design focused on the KPI’s during the monthly conversations and describe weekly results in our Monday Morning meetings. We had established a set of 4–5 indicators that predicted success — that formed the heart of the conversation. And, that focus made all the difference. Here are some key takeaways:

Six Months. At the beginning we knew that our teams might suspect that using a new format to discuss coaching might just become the flavor of the month — the product of an erstwhile executive reading a Harvard Business Review article and then quickly rolling out the new program du jour. The response I imagined would be ~we might wait this management fad out if we play along for a few months. We anticipated this might happen. But we played the long game. Of course, some of my direct reports likely thought I would run out of enthusiasm for the model as well. I knew my role. I had to keep everyone focused.

We created a roll out schedule for the entire process — the purpose, framework and expectations. We primed the delivery by region wide calls explaining the process. Steve Johnson spoke with the entire regional organization and he followed up with the second level managers (Region Sales Directors) multiple times to ensure they understood the critical pathways and anticipated any challenges to the new habit.

Over the course of six months, we saw buy in develop almost completely. We also witnessed the sales managers coming to the conversations better and better prepared, anticipating comments from their managers and primed to talk about both their challenges and successes. I reviewed aggregated responses every month with my team individually. At the time, we collected all the responses on excel, and I reviewed each team on specific tabs. Using excel enabled us to aggregate all the numerical data which we converted into charts used to develop a set of patterns and correlations. We built out one series that measured specific activities and tied it to quoting behavior. We tied another measure to sales momentum and yet another to both our recruiting and commercial pipelines. Once again, the key behavior linked Key Performance Indicators to outcomes. If you have access to a really good sales CRM, all of this might appear old school. I agree. Better technology will make the access and use of data easier. But, you still need to work the process.

Results. We started the process in earnest in 2014 and started to see immediate results. Over the course of the next five years, we could directly tie our KPI performance to outcomes. We measured sales performance over four core revenue lines. And, over the course of 2015 to 2019, the region’s average percent to plan measured 103, 144, 120 and 96 respectively in those core lines — in order of importance. The first two revenue lines made up 90% of the new revenue for the region. Please keep in mind that in the major revenue line, in the last two years of performance, the team was +30% to Prior Year. The other revenue line of business fared even better sporting a 109% CAGR, but was aided by startup mode. In any event, we performed against aggressive goals!

Now, you would not credit the new coaching model alone for the consistent performance. The other regions performed well during the time frame. But we performed consistently well across all the portfolio metrics over time. We displayed consistent performance — and that characterized my intense focus on working a model that would meet annual challenges and perform across objectives. Equally important, the KPI’s forced a discipline on our employee agent recruiting where we met our plan — and the was the only region to do so — every single year.

We served as a pacesetter for process improvement in another line of business. And, in that revenue line, we tripled our absolute new premium output over three years. Again, the other regions performed well during this time frame. I don’t want to discount performance across the board — I’m tying a link to our strategy, the very fundamental coaching model, discipline and our turnaround in performance.

Incidentally, we also implemented a unique associate development program (Develop U) and management model (Metrics Mondays) during the same time frame that I’ll address in later posts. Briefly, the development program combined multiple features including a Master Class Series presented by anyone with domain expertise in the region, a meaningful Book Club program, Meditation and a Mentor program. And the entire sales organization deployed a brand-new sales model designed to leverage Insight Selling and harness the power of persuasion methods based on modern neuroscience (emotion + logic.) We rolled out that new model in Summer 2016 and correlated a jump in performance tied directly to that effort in two of our lines of business. So, other factors helped to define our progress.

The coaching process served to amplify other factors as well. Our pricing improved in multiple states over the course of the four-year time frame — as did our ability to pursue other strategies. However, for anyone that knows P&C Insurance, you know that 2017 presented an underwriting crisis. I’m convinced this model helped keep us focused as we designed KPI’s tied directly to outcomes we expected to see during that time frame to aid actions intended to improve profitability. In any event, the model amplified the truism about the value of consistent, disciplined, focused and authentic coaching. And, at the time, it clearly turned our regional performance around. It helped build predictability, discipline and mobility into our leadership — not to mention continue the invaluable practice of authentic conversations in a supportive coaching framework. And, it helped me sleep better!

What does any of this have to do with Sugar High Motivation? Stay Tuned.

Joseph Rupp

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Joseph Rupp
Joseph Rupp

Written by Joseph Rupp

I focus on how to effectively imagine, create and sustain individual and team transformation.

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