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Pushing back on the boss - why it’s important and and how to do it right

One of the trickiest aspects of work is how to challenge upwards. Pushing back is relatively straightforward among close teammates and peers, but can feel risky and even career-limiting when directed upwards. Drawn from my own experience directly advising multiple CEOs and ministers over 20 years, here are 7 reasons why senior leaders need pushback, followed by 7 ways to do it right.

7 reasons why leaders need pushback:

  • Blind spots: Dunbar’s Law says the population limit for most people to function effectively is 150. Leaders often find most of their 150 is made up of other leaders, leaving limited space for inputs from other colleagues.

  • Groupthink: a leader’s known preference tends to generate endorsements while critics are still thinking how or if to raise an objection. This can produce a clear but shallow majority support that can quickly degenerate into groupthink.

  • Flattery: it’s psychologically more pleasurable to agree with the boss than disagree, particularly if a primary driver is one’s career.

  • Haste: leaders’ time is short and there's a premium on making decisions quickly. This can disadvantage those who fear slowing down the process by expressing doubts.

  • Conformity: Solomon Asch’s experiments in the 1950s showed how deep our instinct is to go along with authority figures, even when we privately and consciously disagree.

  • Safety-first: there’s comfort in being part of the group, as a decision that turns out wrong bears little personal responsibility. In contrast, accountability is clear and direct for any individual raising an opposing voice.

  • The boss is not the customer: it’s an understandable temptation to measure success by the mood of the boss. That’s a nice-to-have, but always a lesser factor than the decision’s impact on the frontline.

7 ways to push back safely and effectively:

  • Feelings over facts: facts can be trumped or dismissed. Feelings can’t. “I’m not sure why but I’m feeling a little unsure/cautious/uneasy about this…”

  • Candid can-do: direct, transparent and honest views command respect when expressed agreeably and with a solutions focus. “I disagree because… I think we can come up with an even better option if we…”.

  • Curiosity: validate the boss’ intention but show curiosity over unintended consequences. “It’s an amazing idea - I love it. I just wonder if we’ve covered all the points you set out at the start…”

  • Balanced question: articulate your concern as a question that recognises the value of the proposal but puts it in a wider context and throws the ball back to the boss. “It’s a tricky balance. On the one side we want to achieve X, yet on the other we’ve also committed to doing Y. Will this proposal do both?”

  • Silence: while everyone else is excitedly sharing high-fives, silent restraint can be a highly eloquent and noticeable response, often earning a direct invitation to speak.

  • Time out: without directly opposing, ask for time to develop the boss’ idea and use it to add in alternative considerations and options. “Great idea! How about we take this away to flesh out and come back to you with a plan?”

  • Feedback not pushback: if time allows, survey your colleagues and come back with strength in numbers. “A lot of people love the idea, but it seems up to half have reservations…”

A final point. Pushing back should be done judiciously - never for its own sake, always out of respect and desire for the success of the team, and accompanied by a graceful acceptance of knowing when to let go. Motivated by those intentions, one’s focus shifts from discomfort to the reassuring and professional feeling of doing the right thing. I hope the next time you need to push back, the above tips might help you do the right thing a little righter. Thanks for reading :)

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