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The path to get out of the weeds

Chase Damiano
22 min read
The path to get out of the weeds

Read this if you wish to reclaim your time and empower your people to execute more. Consider this the ultimate guide to getting out of the weeds.​

At the beginning of my coaching career, I set out to devise a system that:

  • Removes the divide between employers and employees. Less “us versus them” mentality.
  • Embeds best practices in leadership and human relationships.
  • Expands leaders’ capacity for self-awareness and personal growth (and make sure the problem isn’t you).
  • Directly addresses the elephant in the room: entrepreneurial burnout and founder mental health.

​The incubation for this method began when I served as a startup COO. Hiring, delegating, training, and creating team results were some of the most valuable skills I learned. Since then, dozens of founders, agency owners, and managers have implemented this method to get results like these:

  • Reclaim 10 hours per week back in their schedule
  • Communicate more effectively and clearly with their teams using a shared language
  • Boost employee engagement, create “a sense of ownership,” and buy-in
  • Grow their leadership confidence

This is for you if you:

  • Have struggled to stay focused on your top priorities.
  • Feel stuck in the weeds and in the day-to-day.
  • Feel you’re not operating at your fullest potential.

The only requirement is that you have at least one direct report (or otherwise someone you can delegate to). You have to have a team to do this.​

The underlying magic at work is by taking these actions, it shifts your mindset and perspective automatically.​

Below is your pathway out. Follow these steps to reclaim 10 hours per week.​

Step 1: Optimize Team Energy

We are always leading by example. We set the bar when we show up clear, refreshed, and energized to perform every day. Being in the weeds, however, can feel like exhaustion, distraction, and quite frankly: running around like a chicken with its head cut off. Your state sets the pace and tone for everything.

The first step is to design a sustainable working schedule and pace to run the team. This begins with you. We are all human beings, and we all have 24 hours within each day, and we can lean on biology to increase our clarity of thinking and maximize our daily energy.

Do this:

  1. Take the AutoMEQ to discover your chronotype (link here). Discover the times of day you’re operating at your peak energy state. (For me, that’s 9am -11:30am and again about 5:30pm – 8pm). At your peak energy level, create a daily calendar block. Call it “Deep Work” or “Focus Time.” Your goal is to put all of the “hard things” you need to do to grow your team in this time block.
  2. Keep a journal with you, and for one week, write down all of your recurring tasks: things you need to do every day, week, month, etc. This could be sales, admin, content, back office, and more.
  3. Write down all of the team meetings you and your team members attend. Write down the purpose of each meeting. If you can’t think of one, permanently cancel it.
  4. Identify the high-yield team meetings you need to capture all synchronous team communication:
    1. Team Sync. Purpose: Review goals, metrics, issues, and actions. Do this 1x per week.
    2. Weekly 1-1s. Purpose: Isolate challenges, create plans, develop talent. Do this 1x per week for every direct report.
    3. Office Hours. Purpose: Solve challenges. Do this 2x per week, then aim to reduce to 0 over time.
    4. Here’s a list of more high-yield meeting types you may need to layer in unique to your business.
  5. Complete the Ideal Workday Planner template (link here, the slides at the end have examples). Visualize and draw out: what would be an ideal weekly team schedule for everyone? Typical optimizations:
    • Identifying common times for the whole team to be “online” together (great for different time zones).
    • Streamlining all team meetings to occur on a single day.
    • Creating “no meeting days.”
    • Remember: You need to protect your Deep Work time. The theory goes: the more time you spend in Deep Work, the more the business grows.
    • Also: It’s likely not everyone will get everything they want. That’s okay. Find trade-offs and commit as a team. You can always change it later.
  6. Write and commit to a team agreement on how to interact with each other throughout the week. Document and agree to statements like:
    • My preferred modes of communication are…
    • I am available and online between the hours of…
    • I expect my team to be available between…
    • Copy me on emails when…
    • Interrupt my Deep Work and get my attention when…
    • Escalate a challenge to me when…
    • Attend our scheduled Office Hours when…
    • Bring me these types of issues in our 1-1…
  7. Block out the daily Deep Work. Schedule the team meetings in accordance with your agreements. Place other recurring tasks at other specific times on your calendar.

Doing all of the above helps you pay attention to exactly where your time is going every day. You’ll feel lighter, more clear, and more motivated just through this step alone. The trick is to get started and stick with it.

Remember the time you created your first personal budget? The first step to drive change is understanding where you’re at today—meaning, digging into your transactions and bank statements to see where your money is going.

Sometimes you may not like what you see. But, keep going.

Step 2: Define Responsibilities

To raise the ceiling, we must first secure the floor.

Imagine trying to build a tall building, climbing higher and higher… but you’re constantly dealing with issues in the flooring. You need to feel confident in the foundation in order to really reach for the top.

To create focus and momentum on vision, growth, the “big picture” and new opportunities (you know, what the team is counting on you to do), we need to secure the floor in our operations.

For those experiencing the issue of being “in the weeds,” the type of work that keeps them in the weeds tends to be:

  • Administrative work, like scheduling, inbox, appointments, invoicing, and basic “to-dos” of running the business.
  • Customer experience, anything from onboarding new customers, to delivery of your product or service (plus the project management of said delivery), to quality control and customer feedback.

Of course, there are other areas unique to each business—but let’s stick to these examples for now.

Do this:

  1. Remember when we wrote out the recurring tasks in Step 1? Organize the tasks into 1-2 key responsibilities that total 10 hours per week of your time. Your goal is to group associated tasks into responsibilities. This is the start of a new part time role for someone on your team.
  2. Identify the new owner of these responsibilities. Likely one of your existing direct reports.
  3. Score each responsibility with the five dimensions in this Responsibilities Scorecard. For each of the five dimensions, give a score of “O” for “incomplete / missing,” a score of “+++” for “fully complete and implemented,” and scores of “+” or “++” for in-between.
    1. Purpose: Is the purpose of the responsibility clearly defined and understood by the new owner? Score this a O, +, ++, or +++. Same as every dimension below.
    2. Success Criteria: Are the metrics and conditions of success defined, documented, and regularly measured?
    3. Process: Is the process or workflow underlying the responsibility defined, documented, utilized, and continuously improved?
    4. Decisions: Are the decisions the new owner can make clearly defined, documented, and followed?
    5. Resources: Are the resources that help the new owner be successful both defined and given?
    6. Impact: With success, how many hours per week do you save? Write the actual number of hours.

We’re breaking down the responsibility into a greater level of detail. This is the upfront work we do to maximize the probability the new owner will be successful in this new responsibility you’re delegating. Think of this upfront work as an “investment” that pays future dividends: your return on investment is 10 hours per week, every week.

Pay attention to where you placed a “+++” on the Responsibilities Scorecard. It means this area is clear and working for you. Celebrate your progress and reflect on what’s working.

Pay attention to your scores of “O” and “+” on the Scorecard. It’s likely this is an area that you’ve gotten stuck in in the past. Maybe you’ve told yourself, “I’m not very good at process” or “I’ve tried KPIs before and they didn’t work.”

We need to dive in a layer deeper to shift these.​

Step 3: Define and Measure Success

Every responsibility needs a clear depiction of what success looks like. Oftentimes, this is where a set of key performance indicators (KPIs) comes in to quantify and measure success. Reducing all of our business to numbers, however, disconnects us from important nuances that are the keys to innovation and change.

Helping your team understand what success looks like reinforces the idea to be outcome-focused. Else, we risk having team members that define success by “getting everything done” instead of creatively thinking and innovating alongside of you. This risk is how bureaucracy compounds within organizations. We want light, scrappy teams that think on their feet. The trick is to define where we are going.

I detailed this out in this LinkedIn post, but here’s the gist.

Do this:

  1. For each responsibility, write out how success could be measured with the following lenses:
    1. Outcomes. What do our customers actually want to do? What is the problem we solve for them? How does this responsibility help us do that?
    2. Feedback. How do our customers perceive our product or service? How do we act on this feedback? How does this responsibility improve our ability to get feedback?
    3. Financials. Is there money in the bank? How does this responsibility influence our financial picture?
    4. Performance. How effective and efficient is our operation? What growth metrics do we need?
    5. Gut. What does our inner compass say? How can we shed light on our internal feelings and sensations in a healthy way?
    6. Process. Are our standards met and complete? This is the world of completing a checklist, submitting feedback forms, getting approvals, and entering data.
  2. From the exercise above, select 1-3 definitions of success above to track and measure.
  3. Choose a target for each of them. This is the performance target you’re asking your direct report to achieve.
  4. Choose the frequency to measure and review measures. Likely add this as a weekly agenda item to one of the recurring meetings you selected above.
  5. Ask the new owner to manually report these numbers prior to the next meeting. Have you ever tried implementing a scorecard, but your team isn’t reporting their numbers?

The result of this step is to get the Success Criteria dimension to be a “+++.”

We’ve now defined a responsibility (or two) that can reclaim 10 hours of week of our time—if we delegate this successfully without sacrificing quality. This is the primary focus of the next step.

The new owner, your direct report, is now getting a stronger sense for the ins and outs of this responsibility. You’ve clarified more deeply what you’re asking them to do.

For your most senior direct reports, this may be all that’s necessary. Perhaps you leave it to them to figure out the details. But for more junior folks, it pays off to proactively define the rest.

Step 4: Align on Expectations

We want our teams to take a “bias toward action” and “move fast and break things.” This means creating an environment where our teams feel confident to make a decision and move forward. You’re empowering them to drive more decisions autonomously—without your explicit approval. This translates into less “back and forth” on menial issues throughout your day.

Remember the Responsibilities Scorecard from above? This is where we take every “O” and “+” and get them to be a “+++.”

We’re empowering our team by sketching the Process to create the success criteria, the Decisions they can make autonomously, and the Resources we can give to help them.

Do it:

  1. List out the major steps (about 3-5) required to create the Success Criteria. Keep it big picture. What has to happen in order to get the outcome? It may look like a project plan or a process outline.
  2. For each major step, write the decision type (below) and the name of the people involved in each step:
    1. Which steps can the new owner complete autonomously (without your approval or feedback)?
    2. Which steps can the new owner complete collaboratively (with your approval or feedback)?
    3. Which steps require your input or decision (new owner cannot autonomously complete on their own)?
    4. Which steps require someone else’s input or decision?
  3. List out the Resources you can give to help the new owner be successful in their new responsibility:
    • People. Your team, other teams, customers, contractors, etc.
    • Software. Databases, automation, workflow, tracking, systems, etc.
    • Budget. Upfront, one-time, recurring, percentages, etc.
    • Time. Hours, days, weeks, months, quarters, years, etc.
    • Feedback / Meetings. Special check-ins to review results, answer questions, give feedback, coach.
    • Training. Detailed sessions on how to execute the Process.
    • Documentation. Additional resources like videos, SOPs, checklists, etc.
    • Rewards. Incentives, bonuses, perks to facilitate transition.
  4. Actually give the Resources!
  5. Set a date for the new owner to begin this new responsibility with all of the clarity you’ve defined. Preferrably, start now (why wait?).

​Setting this up helps establish the “rules of the game” for the new responsibility. We’re not defining explicitly how to do everything—that’s where we need the creative help of our team. This is part of why we’ve hired smart people—to help us get things done at the next level of their growth. We’re merely defining the goals and the support tools to get there.​

Step 5: Coach To Results

We’ve set up the system—then we press play. Inevitably, the new owner will have questions, get stuck, and need help. In the old paradigm, whenever an issue arised, you dropped everything you were doing to help. In the new paradigm, you’ll redirect all questions and requests for help into one of the recurring meetings (Team Sync, 1-1, or Office Hours). This is a part of the team agreement you created with them.

Do it:

  1. When the new owner gets stuck or asks you a question, redirect:
    • “Great question. Could you add this as an agenda item to our 1-1?”
    • “Happy to help you dig deep. Would you join me for Office Hours later today so I can see what you’re talking about?”
    • “This sounds like a great discussion to have in our next Team Sync. Please add it to our agenda so we can prioritize it.”
  2. Prior to that next meeting from above, ask the new owner to frame the problem with the following questions:
    • Describe the Problem: Describe the problem in 1-2 sentences. Be specific and concise.
    • Cost of the Problem: What is the cost of the problem?
    • Information Missing: What information are we missing to define the problem better?
    • Describe the Outcome: What is the desired outcome, were we to solve this problem? Describe in 1-2 sentences. Be specific and concise.
    • Benefits of the Outcome: What are the benefits if we get this desired outcome?
    • Blockers/Risk of Change: What are the blockers or risks of change?
    • Three Possible Solutions: Write down three different approaches to solve this problem. Limit the number of words to 10 per solution. Be concise. Recommend one of the three.
    • Resources You’re Requesting: In order to implement your recommended solution, what resources or additional support do you need?
    • Recommended Next Action: Write down one discrete and concise action you can take to move forward on a solution.
    • Also: You can get all of this in a template with the Infinite Coaching Framework. Check out the speaker notes for detailed descriptions on each question. Hand this to your new owner.
  3. Ask the new owner to present their answers to the Infinite Coaching Framework in the meeting. In this meeting, your role is to:
    1. Help them clarify the components of the framework.
    2. Actively listen and confirm understanding of their situation.
    3. Ask questions to encourage deeper thinking.
    4. Share feedback and input with discretion.
    5. Help them commit to the next actions they need to take.
    6. Hint: If you’re talking more than 20% of the time in this meeting, talk less and ask questions more.

You are enabling the new owner to resolve challenges related to the responsibility you delegated. We delegated the full responsibility—meaning, you’re counting on them to complete every facet of that responsibility, through and through. But of course, new owners do not get 100% everything right on day 1. Neither do you. So, we’re adopting an approach that is committed to their learning—and eventual full ownership of the responsibility.

To do this, we have to allow our teams to struggle with the challenge a bit. We do this every day in entrepreneurship. Our role as leaders is not to solve every problem that appears; our role is to develop our people. The strategy listed above encourages more critical thinking, problem solving, and being a self-starter—all the things we prize in our teams.

Asking the new owner to sketch out their thinking in this way also helps you have pinpoint precision into where you can support them—without getting caught up in the narrative. You’ll quickly see where they are getting stuck in the problem, so you’ll deliver more targeted coaching. You’ll both get more done in less time as a result.​

Getting results

The final step: Every week, measure the number of hours you’re spending on Deep Work. You’ll see this trend up over time. That’s more time for growth. If it isn’t trending up, consider which one of the steps above needs a bit more attention.

By following this approach, here’s what happens:

  1. You and your team have more energy and motivation. You get more growth-oriented priorities done (because you’ve aligned your schedule to your biology and carved out time for daily Deep Work).
  2. You and your team have agreed to take new responsibilities off of your plate to free up your time AND give them opportunity to grow.
  3. You have a system to monitor and celebrate success AND dig into issues as they arise.

Continue this system. Iterate and play with it. Find ways to make it more efficient and unique to you and your business.​

We’ll continue our journey exploring these topics in the future.​

Where can I help and show you more? I’d love to hear from you.

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