3 Ways to Tactfully Challenge the Boss

Jessica Tiao
3 min readAug 25, 2023

Disclaimer: These are my notes on the Harvard Business Review Podcast: Challenging the Boss.

#1: Boss gives cruel, unhelpful feedback.


The boss forgets updates and criticizes. It leaves the team frustrated and demoralized. The team also feels micromanaged and a feeling of failure.

Solution #1:

After a meeting, write an email recap:

Boss, you’ve specified, we are handling the following 3 things:




Solution #2:

When a manager is not paying attention or thinking through feedback, it’s disruptive. Take the project, but get barely started with the project and check-in.

Boss, we’re thinking in these directions:




How does this match with what you’re thinking?

Solution #3:

Have a direct, indirect conversation.

Boss, how can we find ways to give input that’s actionable, useful so the team has autonomy and the team feels they are doing a good job?

Solution #4: Call it out.

Boss, I don’t think you realized that when you gave feedback of X project, it didn’t come across very well. I’m sure you didn’t mean to hurt her feelings. I wanted to let you know it’s happening.


Create mechanisms such as

  • Draft submissions
  • Send follow-up emails/Slack messages
  • Check-in often
  • Document Conversations

#2: Boss starts calling you and emailing to take on extra projects


Jack tried to set up boundaries. Jack’s step-level boss (Jack’s boss’ boss) calls Jack because Jack isn’t responding to emails. Jack is asked to take on an extra set of responsibilities. Jack expects recognition or reward. Jack wants to look good. Boss is bringing on more work.

Let’s breakdown the problem:

  • Jack might work at high intensity workplace where employees are always on 24 hours of the day.
  • There may be a mismatch of expectations.
  • It feels like a violation of boundaries, but also, being reached out to on the weekend is a good sign.

Solution: Prepare a positive mindset

  • Do not assume bad intent.
  • Don’t act like a victim
  • Don’t complain
  • Don’t be resistant.
  • Act engaged and happy.
  • Put in soft rules.
  • Show interest in being involved.


  1. Get advice from boss on how to work with the boss’ boss.
  2. Have boundary setting conversations.
  3. Step-up and do it. Participate and be of value.
  4. If a phone call from co-workers feels intrusive, shift the communication to emails. Clearly communicate to the boss’ boss to stop phone calls.

#3: Your boss is fired/laid-off. Training falls on you, and the team is worried about layoffs. Your boss wants the team to try a new approach that sounds problematic to the team.

Let’s breakdown the problem

What a tough spot to be in, it’s a layered problem:

  • New executives are not fully acquainted with the business of the organization. They do not have full understanding of: How does it actually work? What are the team’s true needs?
  • “The training fell on me. Worried about layoffs.”
  • No one wants to say, “That’s not the way we do it.”


  1. Position yourself as an ally to the boss.
  2. Have a semi-formal conversation to understand the boss’ goals?
  3. Is it the work of the department? Or, is it an extra-curricular activity?
  4. Make a mental transition: Grieve the old boss. Welcome the new boss. Acknowledge that there’s an emotional component.
  5. Have broader collaboration as a team so that one person on the team does not feel burdened by enlisting the team. There’s an opportunity because the team is ready to leave. With a merger, employees feel unsettled and nervous.
  6. Talk about the merger. What’s happening? What are the implications of a merger? How can everyone move forward?
  7. Let’s make a plan as a team. What’s working? What’s not working?
  8. Let’s have a discussion as a team about the extra projects.
  9. Taking on extra work is an increase in value, an increase in visibility. Is it being communicated to the team?


It’s hard to speak up if a boss is unhappy with you. Confronting people gets scary. How do we bring necessary information to the boss so everyone can bring value?

  • Work on specific behaviors.
  • Strengthen relationships.
  • Shift mindset: embrace the challenge
  • Position self as an ally
  • Understand: What are the goals?
  • Discuss work on your plate, align on the priorities, how and when work gets done
  • How to offload the work? (if that makes sense)



Jessica Tiao

Sr. Product Designer @Twilio. Past lives: Crazy Egg, Kissmetrics, Tradecraft. Puppy and llama fanatic. Star-gazer. @JessicaTiao, www.jessicatiao.com