Navigating the Dilemma: Providing a Reference for a Difficult Former Boss

Finding oneself in a situation where you are asked to provide a reference for a former boss can evoke a whirlwind of emotions. Recently, I encountered this conundrum, and it felt oddly gratifying to have the upper hand after my challenging experience. Here’s my story and some thoughts on how to gracefully handle such a request.

The Backstory

In my previous role as Controller for a private equity-backed startup, I experienced the vibrant startup culture alongside dedicated colleagues and a commendable product that I genuinely believed in. The compensation and work-life balance were also noteworthy perks. Unfortunately, the one significant drawback was my boss—the CFO.

This individual, who lacked operational wisdom and appeared to fluctuate between micromanaging and disappearing when needed most, was a continual source of frustration. His background in private equity led to a disconnection from the operational needs of our team.

The situation came to a head when he missed a critical meeting and expected me to accommodate him at an unreasonable hour with little notice. After multiple attempts to work through these challenges, the stress became unbearable, eventually leading to my resignation followed by his termination just six months later.

The Unexpected Request

Despite the distance since my departure, I recently received a confidential email from a recruiter seeking “informal feedback” about this former boss. This unexpected request opened the door to a dilemma: How do I respond honestly while remaining professional?

What Should I Say?

When faced with the choice of providing feedback, it’s essential to consider the implications of your response. Here are some pointers that balance honesty with professionalism:

1. Stick to the Facts: Share your experiences based on specific situations. Highlighting operational struggles without venturing into personal allegations can maintain professionalism.

2. Be Constructive: Instead of simply outlining negatives, suggest areas for improvement. This could provide a more balanced perspective.

3. Consider the Bigger Picture: Reflect on how your feedback might impact the person applying for a new job. Is your goal to be vindictive, or can you contribute to a positive change in their future performance?

Should I Inform My Former Company?

You might also wonder about notifying the company about the CFO’s job search. This decision ultimately hinges on your perspective and circumstances. If you believe his departure would significantly benefit the organization, considering an anonymous tip could be an option. However, weigh this carefully against potential repercussions for yourself.

In