Feedback is a gift, With the right intention it can help you stay on target, get back on target or lean into a new target. Done well feedback, avoids the amygdala hijack, and "lands" with the individual receiving it helping them grow and develop.
Done manager-to-subordinate, peer-to-peer it can be challenging but a skill we can all develop and refine. So how then do we give feedback up into the organization to our manager or a senior leader? As a coach I regularly sit with clients and discuss this very topic and here are several of the most frequent ideas they develop.
Contracting with their manager: At their next 1-1 ask the question " how challenging do you want me to be?" This is better than asking "can I give you feedback?" as you and they likely have a different view of what feedback is, by asking them how challenging you can be you are signaling you want to challenge but also want to be respectful. Bonus idea for this time of year, you might ask the "how challenging" question in your performance review.
Knowing when the best time to give the feedback is also important most clients know the high pressure events in their leaders week and avoid immediately before or after. Also where can be important, one client suggested a walk and talk meeting - the combination of neutral territory and natural environment (they walked around a marina) created a space conducive to comfortable silence and minimized distractions.
Word choices (linked to messaging below) are there words or phrases that will resonate or trigger them? what are they and how can you use or avoid them?
Messaging: Linking the message of the feedback to the values, drivers and motivators of the leader is another useful approach. Are they concerned about image, the perception of others? Do they think in terms of legacy? Finding the angle that links your message to what is important to the leader helps the message land and be heard.
Sometimes they tell me that it's too hard, that they can live with it. That's the point we contrast that idea with their values and beliefs. And every. single. time they decide they can't live with it.
Giving your boss or a senior leaders feedback is hard, but it beats the alternative.