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Six Tips For Managers From The World’s Leading Startup Coach

This article was based on episode 111 of The Modern Manager podcast. To hear this episode, and many more like it, you can subscribe to The Modern Manager Podcast on iTunes, Google Play, Spotify, iHeart Radio and Stitcher. Get 20% of The Modern Manager’s Guide to Effective Delegation when you become a member at Purchase a full episode guides at

Across the board, from executives and CEOs to managers at all levels, Alisa Cohn - the world’s top startup coach - hears certain questions asked again and again. Topics of structure, communication, delegation, and power dynamics are essential and often confusing regardless of experience and seniority. To help make sense of these, Alisa shares the top six critical things managers need to understand in order to succeed in the modern workplace.


If you don’t want to spend your entire week responding to email, you and your team need to establish “strategic thinking time” to plan out your schedule. Without intention, our important, but not urgent, work typically falls to the bottom of the list. To make progress each week, Alisa suggests the following:

  1. Create a rhythm. Establish a regular day and time - ideally Sunday or Monday for an hour (minimum) - to think about all the projects you are working on.

  2. Prioritize for the week. During that thinking time, decide which one or two projects are the most important for you and what you need to get done for each.

  3. Schedule time for your priorities. Add events to your calendar to block time when you're going to make progress on those things.

  4. Ensure your team is thinking, too. Make sure that your employees do the same. Encourage them to schedule ‘strategic thinking’ time and/or set a weekly check in to review priorities and progress together.


Across the board, leaders generally don’t realize the effect of their positional authority as “the boss”. Whether they want to believe it or not, trivial comments carry a lot of weight for their direct reports. When a boss suggests an idea to their team it can come across as an order. When a leader asks out of curiosity, “How come you guys did that?”, many employees hear an accusation. Often, team members mistake an idea thrown out by their superior for a directive, and feel high stakes to execute on it immediately, wasting a lot of time from this simple miscommunication.

Alisa suggests consciously communicating so that your remarks comes across as discussion and not an order. To do so, try:

  • Intentionally softening your tone. If you’re high energy or tend to be very stoic, consider shifting your energy to find a more casual note.

  • Use more words and elongate your sentences, to lessen the directness of your response, i.e., “I was wondering if you had thought more about these kinds of ideas.”

  • Be explicit about your objective of the conversation. If you’re brainstorming, say so. Explicitly decide who takes what role so there is no confusion. Verbalize a decision or lack of the decision as you see them: “I’m not sure we're ready to make a decision. Let’s have another conversation after we digest what we spoke about today.”

  • Build up a sense of psychological safety on your team. Show yourself not as a punisher, but as an obstacle remover and an ally, someone they can talk through their problems with who wont fire or snap at them for making a mistake.


Many meetings end with a false sense of alignment. There’s been an hour’s worth of discussion and some decisions made, but exactly what was agreed to isn’t fully shared. Regardless of whether it's a small or large group meeting, it’s important to end the meeting by asking, “What did we decide here?” and “Who is going to do what by when?” This ensures alignment and understanding so right things get done.


Delegation is not about your managerial style, preference, or how hands on/off you want to be. It’s actually about what your employees need from you to succeed. To delegate well, Alisa encourages breaking down the different elements of the assignment by thinking through few key areas before you hand it off.

  1. Skill and will. What is the person’s skill and experience with this type of project, and how willing are they to do that kind of task?

  2. Ability to quickly uptake the task. Do they need a lot of instruction? Are they more junior and inexperienced? Do you need to break it down for them to help them understand the task?

  3. What does “done” look like. You need to have a clear idea in your own mind about what you want the end product to be before you hand it off. Once you’re clear, you must communicate this vision fully.

  4. What’s the timeline. Did you agree on a deadline? Share why this timeline matters.

  5. When will you check In. Will there be a mid-course check in to assess progress and answer questions? How will you address confusion or issues along the way?

  6. Share the full picture. Did you give context for the project and ask what elements of it they wanted to do, or did you give a directive? Gopher-style micromanaging reduces morale and incentive. Empower your employees by giving them the full picture of what you’re trying to do and ask for their specific interest in involvement.


There is no magic formula for when to give more or less autonomy to your staff. Healthy autonomy requires agreement between a manager and each team member on how much oversight they desire and their strengths and weaknesses for autonomous work. Alisa recommends holding individual discussions as you try to assess how involved you need to be with each person.

In addition to these conversations, examine the experience levels of your employees. Try to best calibrate how much direction vs how much leeway each person needs to perform well and grow. The more the person feels comfortable coming to you when they need help, the easier it will be to provide greater autonomy.

The only way you will know if you need to have more oversight on an employee is by learning as you go. Set up the context and see how the person does. If they are confused by the project and need more help or feedback, provide it. If they come back with a completed job well done, they’re ready for more independent work.


Even though working from home has become the new normal, we haven’t all mastered it. If you haven’t yet (or recently) spoken with each person about their work situation, Alisa suggests having an in-depth discussion to ensure they are optimizing their remote work situation. Include the following in your conversation:

  • Workspace: Do they have their own workspace? Is it comfortable for them? What might your company be able to provide them to make them more productive? Can they take anything home from the office building e.g. computer monitor or desk chair?

  • Schedule and Breaks: What are their “office” hours? Are they taking breaks every 90 minutes or so to move around and clear their head? How might you help them create focus time?

  • Have Guidelines For Technology: As you’ve become more reliant on virtual tools, you may be finding they’ve become overwhelming or used inconsistently. Agree to team practices for chat tools, email, task tracking, document storage, etc.

It’s the simple but powerful elements of communication and structure that create a cohesive team dynamic. A leader’s thoughtfulness about time, tone, and autonomy for each individual team member allows for teams to thrive at the personal and collective level. Alisa’s simple guidance will help build habits for managers across all types of organizations and companies.


Get 20% off The Modern Manager’s Guide to Effective Delegation when you become a member of the Modern Manager community at

This article was based on episode 111 The Modern Manager podcast. To hear this episode, and many more like it, you can subscribe to The Modern Manager Podcast on iTunes, Google Play, Spotify, iHeart Radio and Stitcher. Never miss a worksheet, episode or article: subscribe to Mamie’s newsletter.




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