The Fine Art of Working with a Flaky Boss: Strategies for Success

How do you tell if your boss is a flake? Having a supportive and reliable boss is pivotal in any professional setting. A boss who consistently follows through on commitments fosters a positive work environment and sets a standard for accountability and trust within the team.

Unfortunately, not everyone is fortunate enough to have such a boss. Dealing with a flaky boss – one who is often unreliable in various aspects of their role – can be a significant challenge. It can reduce workplace morale, increase stress, and hinder professional growth.

In this article, we’ll explore the various ways bosses can be flaky and provide actionable advice on effectively working with them, turning these challenges into opportunities for professional development.


1. How do you work with a flaky boss who constantly reschedules meetings?

Frequently showing up late to meetings or constantly rescheduling them disrupts the workflow and indicates a lack of respect for others’ time. Here’s how to work better with a flaky boss who shows up to meetings late or constantly reschedules them:

  1. Initiate a Scheduling System: Propose a shared digital calendar where meetings are scheduled, allowing you and your boss to have a clear view of each other’s commitments.
  2. Set Clear Agendas: Before each meeting, send a brief agenda. This can highlight the meeting’s importance and encourage punctuality.
  3. Offer Flexibility: Understand that emergencies happen. Offering flexibility and alternative slots for rescheduling can foster goodwill.

How do you talk to your boss who constantly reschedules meetings?

Example 1: “I’ve noticed that our scheduled meetings often get shifted or start late, and I’m concerned about how this impacts our project timelines. Could we discuss how to improve our scheduling to ensure we’re both on track?”

Example 2: “I wanted to talk about our meeting schedules. I feel that the frequent changes are making it challenging to maintain momentum on my tasks. Can we explore a more consistent schedule or set fixed times for our meetings?”


By initiating a conversation with your boss tactfully and with understanding, you can bring attention to the issue non-confrontationally, paving the path for a more structured and respectful scheduling process.

2. How do you work with a flaky boss who doesn’t fulfill their promises?

A boss who often fails to do what they say they will can lead to mistrust and hindered project progress. Here’s how to handle a flaky boss who doesn’t deliver on their promises:

  1. Document Commitments: Keep a record of commitments made. This can be referred to in follow-up communications.
  2. Gentle Reminders: Send polite reminders via email, listing pending items and their impact on project timelines.
  3. Seek Clarification: Sometimes, a lack of follow-through stems from misunderstanding. Clarify expectations during discussions to ensure alignment.

How do you tell your boss they aren’t following through on their promises?

Example 1: “I’ve noticed some challenges we’ve faced with meeting project commitments. I believe addressing this could greatly enhance our team’s efficiency. Can we discuss potential strategies for ensuring our commitments are fulfilled?”


Example 2: “I wanted to bring up a concern regarding some unmet commitments impacting project timelines. We need to understand how we can better align our expectations and follow through. Could we set aside some time to talk about this?”

Approaching your boss with concrete examples and a constructive tone can open up a dialogue for improvement. It’s about fostering a culture of accountability and support rather than assigning blame.

3. How do you work with a boss who is an unresponsive flake?

A boss who doesn’t respond to emails unless others are copied can create communication barriers and slow decision-making. Here is how to work with a flaky boss who doesn’t respond to emails:

  1. Effective Email Techniques: Use clear subject lines and bullet points to make your emails concise and actionable.
  2. CC Strategically: If necessary, include other relevant team members to encourage a response.
  3. Alternate Communication: When your flaky boss consistently ignores your emails, seek alternative communication methods like brief face-to-face check-ins.

How do you talk to your boss about their unresponsiveness?

Example 1: “I’ve noticed that some of my emails don’t receive a response unless I include others. I’m concerned this may lead to misunderstandings or delays. Could we discuss how we might streamline our email communications for more effective collaboration?”

Example 2: “I wanted to address an issue I’ve been encountering with email communication. It seems my messages often go unanswered unless they’re more widely circulated. Can we explore ways to ensure direct communications are also acknowledged and responded to promptly?”

By addressing the issue directly yet sensitively, you can encourage your boss to reflect on their communication style and its impact on the team. This conversation is an opportunity to establish more effective communication practices that benefit everyone involved.


4. How do you work with an absent boss?

A boss who is not regularly available or reachable can lead to feelings of isolation and lack of guidance. Here’s how to work with a flaky boss who is rarely available or constantly absent:

  1. Establish Regular Check-ins: Propose a regular, brief check-in meeting to stay connected and updated.
  2. Use Written Communication: When face-to-face communication is challenging, rely on detailed emails or instant messaging for quicker responses.
  3. Self-Initiative: Without regular guidance, take the initiative to make decisions within your scope, documenting them for later review.

How do you talk to your boss when they are unavailable or unreachable?

Example 1: “I’ve been finding it challenging to get the guidance I need due to our differing schedules. Could we discuss a way to establish more consistent communication channels that work for both of us?”

Example 2: “I wanted to talk about how we can improve our communication. There are times when I need your input but find it difficult to reach you. Can we explore some solutions to ensure I have the support needed to move forward effectively?”


Initiating this conversation shows your proactive approach to finding solutions and underscores the importance of consistent communication for effective team functioning. It’s an opportunity to establish new norms to enhance your performance and your boss’s overall dynamic.

Transforming the Challenges into Opportunities

Working with a flaky boss certainly presents challenges, but it can also be an opportunity for growth with the right strategies. By implementing these actionable tips, you can foster better communication, enhance your problem-solving skills, and develop greater independence and resilience in your professional life.

Remember, the goal is not just to cope with a flaky boss but to thrive despite the challenges they cause, turning potential setbacks into stepping stones for your career advancement.


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Jason Cortel is currently the Director of Global Workforce Management for a leading technology company. He has been in customer service, marketing, and sales services for over 20 years. In addition, he has extensive experience in offshore and nearshore outsourcing. Jason is an avid Star Trek fan and is on a mission to change the universe by helping people develop professionally. He is driven to help managers and leaders lead their teams better. Jason is also a veteran in creating talent and office cultures.

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