What Do You Do When You Don't See Eye To Eye With Your Boss?
I once worked for someone named Ted, who was sharp, ambitious, and hardworking. He expected a lot from his team. None of this was problematic for me. However, as we continued to work together, points of divergence began to emerge. Ted wanted to do a lot at once and had unrealistic expectations about how quickly the team could deliver his agenda. At the same time, he impeded decision-making, slowing progress despite his desire to move more quickly. He didn’t cope well with negative news, leading people to hide issues from him. He also had a tendency to tolerate bad behavior when the outcome suited his needs, in conflict with the organization’s values. In all, these factors created a working environment in which I felt increasingly uncomfortable. Ultimately, I moved on.
To be clear, being completely in sync with your boss is a rare and fantastic thing. You might never experience it, and by and large, you should expect to see both positives and negatives in each of your managers. You’ll need to take a balanced view and not expect perfection or complete alignment. Otherwise, you’ll likely never be satisfied. As a consequence, you won’t always see eye-to-eye with your boss. Some of these situations will be temporary, and others more sustained. You might disagree on certain things, but have enough alignment otherwise to maintain a constructive working relationship. What becomes more challenging, however, is when the differences run deeper, relating to some combination of strategic direction, operational approach, working style, leadership philosophy, or personal support.
When you and your boss aren’t seeing eye to eye in a way that truly matters, it creates a ripple effect across your workday – clouding your focus, sapping your motivation, dragging your team down, and making you second-guess yourself. These are uncomfortable situations, especially when the dynamic feels strained or unclear, and the circumstances persist. However, such conflicts don’t necessarily have to result in an insurmountable roadblock or an endgame, as mine did with Ted. In many cases, they can be a turning point and an opportunity to build alignment.
So, before you say anything rash or make a snap decision in these situations, pause long enough to take a breath and reflect. Stepping back allows you to consider what’s really going on, especially when you feel misunderstood or dismissed. In the end, you have several options:
Not every conflict will resolve easily, and some may not resolve at all. If the disconnect begins to affect your performance or well-being, you may need to loop in a third party, like your manager’s own boss or HR. However, regardless of the outcome, how you handle these situations will say a lot about your professionalism and may open the door to a stronger, more productive working relationship with your manager. If it doesn’t, and you ultimately decide to move on, accept that doing so be healthier for you than remaining where you are and rotting from the inside.
JR and the PathWise team
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Recent and Upcoming Podcasts
September 15 – Championing the Small Business Underdogs, with Sri Kaza. Sri is a seasoned business leader and small business advocate. His new book, Unconvention: A Small Business Strategy Guide, draws on this extensive experience in working with small businesses, challenging them to shed conventional corporate thinking and empowering them to succeed by staying true to their unique strengths. In our discussion, we’ll cover the key lessons from Sri's book and his own career journey.
September 15 – Championing the Small Business Underdogs, with Sri Kaza. Sri is a seasoned business leader and small business advocate. His new book, Unconvention: A Small Business Strategy Guide, draws on this extensive experience in working with small businesses, challenging them to shed conventional corporate thinking and empowering them to succeed by staying true to their unique strengths. In our discussion, we’ll cover the key lessons from Sri's book and his own career journey.
Recent and Upcoming Members-Only Content
September 15 – Values. Whether at the organizational or personal level, values define who you are and what's important to you. But they need to be more than words on a page. They need to be lived every day. We'll cover how to define and honor your values as part of this week's focus.
September 22 – Roles & Role Clarity. A team with unclear roles is like a group of five-year-olds playing soccer (football). Everyone is running around, seemingly busy, but not getting nearly enough done that really matters. We'll share guidance on how to create clear roles, whether in a day-to-day or project capacity.
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September Book Summary
September Book Summary – Dare to Lead, by Brene Brown, presented by PathWise’s Daniela De Luca. Brown's TED Talk on shame and vulnerability is one of the most watched talks of all time. In her broader work, she has become a leading voice on personal growth and connected emotionally with millions of people. We'll cover the application of her core beliefs in the realm of leadership in this month's book summary.
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