Managing your Boss – Risky Business

One of the toughest jobs a leader can take on is leading horizontally and leading up. Leading without authority or the power of title is a critical skill that all great leaders have learned. Even a CEO has to, at times, lead the board of directors or the Chairperson needs to lead shareholders. To develop this lateral and upward leadership is when a leader must exercise his/her determination, resolve and courage but also must demonstrate their compassion and situational awareness. To illustrate this skill, I’ll tell a story.

A young, entrepreneurial company had a winning business model that was being proven and successfully monetized. They had successfully raised an angel round and were setting the stage for the Series A round. A recent hire, while putting the pitch deck together and analyzing the income and expenses of the company, discovered a problem with the costs. Significant expenditures were being paid to third parties that did not have an apparent connection to the company. Upon a more in-depth examination, this employee realized the Founder was paying personal expenses from the company income and not reporting it as personal income.

The Founder had a reputation of being very volatile and even vengeful to people he felt had treated him wrong or crossed him in any way. The company held great promise with a huge upside for this employee, but she also knew this behavior was not appropriate especially after the Founder brought in angel investors as partial owners. Since this employee was brought in to raise this venture round her reputation and credibility were also at risk. What did she do with this moral dilemma? She met with the Founder to address her discovery and to understand better the true nature of these expenses. Her worst fears were realized.

The Founder was using company money to pay personal costs. His justification was, “It’s my company. I am the Founder, CEO and President and I’ve got a lot of ‘skin in the game'”. The Founder was reminded that the minute he closed on the Angel Round, it was no longer his company but a company of many and he was not entitled to use money personally without proper documentation, plus there was the issue with adequately reporting and paying payroll taxes on his entire income. This employee then indicated that the only way to correct this payroll and accounting problem was to amend past income tax returns and immediately pay the outstanding payroll taxes on this income that had been previously unclaimed. We can all imagine the risk this employee took in taking on this conversation. Would you have had this resolve and courage to demonstrate this level of leadership? The threats were significant for this employee. She knew she might be immediately terminated and the upside of this company’s enormous potential would be lost. However, she also knew that as an employee of a closely held stock company and the point person in raising the next round she had a greater responsibility to the company than to a badly behaving CEO. It takes real courage to lead up, but it also takes a robust and unwavering acknowledgment of your core values – that commitment to do the right thing regardless of the consequences. Luckily the leading up we may be called upon to do in our jobs isn’t fraught with the same extreme risk of this example, but it doesn’t diminish the perceived risk we feel in our daily leadership interactions. Although the risks may be less severe, there is one crucial step in leading up and horizontally that we must take.

After this leadership encounter and after a short time for the person to get some distance and perspective on the encounter, check in with them; I call it “checking in for wellness.” Helping them with an important behavioral or course correction is one thing but checking in for their personal and your professional relationship wellness is essential. This step doesn’t have to be a big deal; it is just going to them without any apologies or excuses and say, “Are you okay? I know yesterday got prickly, but I value our professional relationship and what you bring every day. “Checking in for wellness” insures when you are leading up or leading horizontally that your motives are less likely to be questioned and will help to rewrite the stories that are being written in the mind of this boss or peer…

About Rich Jones

Strategic consultant and Keynote Speaker, Rich brings a deep experience in the disciplines of Strategic Planning, Marketing, Business Development, Digital Transformation, Data Utilization, Leadership Development and Cultural Alignment. A husband, father, runner, cyclist, beer drinker with a passion for life.


  1. Anthony Demangone on July 17, 2013 at 11:31 am

    What a great post! (And blog.) Thanks for sharing.

    • rich0747 on July 17, 2013 at 5:02 pm

      Thanks for the feedback!

    • rich0747 on August 2, 2013 at 5:27 pm

      Thanks for the follow and nice comments.

Leave a Comment