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Let’s start with the premise that most of the time it is in your boss’s interest for you to succeed. When that’s true, it is in your best interest to help your boss help you. This is not about doing your boss’s job for them or asking them to do your work. It is about taking a disciplined approach to helping your boss review your work, provide insights, and help you move things forward. Do that by 1) Clarifying what you’ve already gotten done; 2) Explicitly asking for their insights, and 3) Pointing them in the right direction to best leverage their clout.
Clarify what you’ve already gotten done on the specific project
Start by bringing your boss up to speed. Assume they’ve most recently been thinking about something other than what you’re working on. Give them a general context – something like, “Want your input on project Y, our effort to ZZZ.” Then tell them what you’ve gotten done to date. Note “what you’ve gotten done” is different than “what you’ve done.” Lead with the headlines of accomplishments. Spare them the details around how you made the sausage.
Explicitly ask for their insights to improve your best current thinking
Different bosses will want different levels of detail on your thinking. Gear your explanation of your best current thinking to their preferred way to take in information. In general, the higher the level of your boss in the organization, the more they’re going to care about strategic and organizational thinking and the less they’ll want direct involvement in operational details. But that’s not always the case.
This is particularly relevant when you’re talking to your boss’s boss. Don’t assume they process information the same way your boss does.
With that in mind, take them through your insights around context, what matters and why, your approach, colleagues and communication and making things happen.
Context
Take them through what you’re thinking about customers, collaborators, capabilities, competitors and conditions. You might pull this together to highlight your key leverage points (strengths versus opportunities) and business issues (weaknesses versus threats.) Your ask here is for insights to improve your understanding, assumptions and conclusions.
What matters and why
Focus here on your objectives and the rationale for why that’s important to key constituents. Your ask here is for your boss to confirm your assumptions or improve on them.
Approach
Approach is about choices. Lay out your strategic, organizational and operational choices with an eye towards spending more time on the types of choices that are most relevant to your boss. Your ask here is for your boss to challenge the options you considered and help you improve your choices.
Colleagues
Help your boss understand which colleagues you’ve brought in to help you with your thinking or implementation so far. Ask your boss to point you in the direction of other people with whom you should connect.
Making things happen
Bring your boss up to speed on your action plans – what you’re going to do next and then later. Ask them for their perspective on your current plans and what else they think you should do.
Point them in the right direction to best leverage their clout
Put your boss to work. Bosses are resources that can help you move things forward. Ask them to do things you can’t do yourself. Most of the time, this will involve resources or connections.
Resources
Your boss, or their boss, will likely have access to different resources than you do. If you need other human, technical, operational or financial resources to accomplish your objectives, and can’t secure them on your own, ask your boss to reallocate them. The essence of strategy is the creation and allocation of resources to the right place in the right way at the right time over time. Reallocating resources is a core part of your boss’s job.
Connections
Sometimes you’ll need human, technical, operational or financial resources beyond what your bosses can reallocate on their own. In those cases, ask your boss to connect you with the people that can reallocate those resources. In this case, best leveraging their clout is about leveraging their influence.
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