Ask senior leaders these questions

Managing up starts with taking the time to understand the leader that you're supporting. After all, you can't adjust your style or habits to best support a boss or senior leader if you don't know their preferences in the first place. So instead of learning by trial and error, if you're working closely with a senior leader or executive for any significant period of time, take the time to ask specific questions to better understand them. Their concerns, priorities, and preferences. This questioning process may seem completely natural if you're newly working together, or perhaps you've been working together a while and are looking to enhance your working relationship. Either way, taking the time to better understand them can prove to be extremely valuable. Consider questions like this. What keeps you up at night about this project? Most senior leaders have specific stresses and points of concern. The more you understand them, the better you can support them by addressing those concerns. What is your preferred communication style? Have you ever met someone who is slow to respond to voicemail, but don't respond immediately to an email. Or someone who ignores an email, but if you send them a text, they hit you right back. Whether it's face to face, video call, phone, email, or instant message, most of us have a preferred communication mode and we tend to appreciate and respond more quickly to those who communicate with us using our preferred mode. But you can't use someone's preferred mode if you don't know what it is. So asking this question is key. What are your workplace or communication pet peeves? Instead of finding out the hard way that your senior leader hates slides with more than three bullets, or that their meeting motto is if you're on time, you're late, simply ask them to share a few of their workplace or communication pet peeves up front. Most of us have them and this gives you valuable insight into their preferences. Are you more of a morning person or a night owl? Do they love 7:00 AM breakfast meetings while the rest of the office is quiet? Or are they much more of a night owl, preferring not to be disturbed before 10:00 AM? Obviously, this intelligence can be so helpful as you make practical decisions about project meeting times or more generally, as you decide how and when to approach them. What are your thoughts on working remotely? Hybrid versus in-person? Many leaders have fairly strong opinions about the best workplace setting. Some feel strongly about face to face communication. Others love a remote structure, and some fall somewhere in between. While I won't go so far as to suggest that you should automatically adopt whichever setup your leader prefers, I think that knowing their preference at a minimum is helpful. This questioning process begins to lay the foundation for managing up with any senior leader, not just the challenging ones. With great leaders, you're not addressing any specific weakness or challenge behavior of theirs. You're simply taking the time to get to know them so you can best support them in reaching their own goals. In my experience, most people don't do this, and that's why busy senior leaders really appreciate the few that do.