How To “Get Out Of The Weeds” Of Your Organization

As we know, it can be really tough – especially for early-stage organizations – to find (or force yourself to create) time to take a step back and look at how the institution itself is doing.

Being stuck in the weeds is a perennial problem — how do I keep my eye on the whole forest when I have to be down on the forest floor fighting my way through the weeds… 

This is BY FAR the biggest challenge the EDs I work with deal with — there is so much work to do in the organization, it can feel impossible to find time to work ON the organization — to think about the organization as a whole. 

So what do I mean by getting out of the weeds? And how do you do it? 

I’m going to give you 3 concrete strategies for getting out of the weeds in your own organization. Two of them I’ve talked about in previous episodes, and the 3rd I’ll walk through here.  So I’ll reference the other two, and have pulled all 3 of these Get Out Of The Weeds episodes together into a little playlist at 


So to start off – I want you to think about 3 types of work that we need to do as leaders: Generative, strategic, and tactical.  Most of our work can be organized into these 3 buckets, and all 3 are important to balance within the organization. 

Think of it like a slope — at the top, is generative thinking and work – 

Big picture: values and vision… what is the organization all about? How are you showing up in the world? What values and principles are important to the work? Are you staying true to the mission. 

This can be the hardest to find time to think about because it feels the fuzziest. But it’s SUPER important in setting the framework for literally everything else that the organization does. 

Middle of slope is strategic thinking and work  — 

This is about how you carry out the mission and vision and values. It’s the level of thinking that turns your vision, mission, etc. into an actual plan. This is where you start to think about priorities, navigate problems and challenges. What will you actually do? How do you weigh pros and cons? What is the best way forward? 

Finally, the bottom of slope is tactical thinking and work. This is about execution — tasks to be carried out, specific steps that need to be taken. This is the level where you’re thinking about the specific policies you need to draft to implement the new approach to crafting compensation that you’ve developed. 

Each of these modes of thinking about the work are important — generative sets the framework, strategic crafts the plan to organize the work, and tactical executes. 

You may find that you spend more time in one as opposed to the other two. That makes sense – most of us are more comfortable with a particular type of thinking and engaging. 

The key is that all are important — They build off of and respond to one another. Let’s say you’re thinking about impact:  How you define it, create it and measure it. 

You have to think at the generative level about whether you want to define true impact on the girls your serve in terms of numbers served or depth of transformation. Breadth and depth require different types of strategies and resource allocation – you can absolutely have both, but the more you move in one direction – for example towards wanting to reach 1000 new students in the next year – the more resource intensive it is to have deep, personal transformation for all 1000. 

So generatively, you need to decide how the organization will define impact. 

Strategically, once you’ve identified the core definition of impact – let’s say it’s breadth – then you need to map out what that means in practice. How will you get to the numbers you’re looking for? What strategies will you use? How will you reach the girls? Through partnerships? Through their parents? Through their peers? What type of engagement will you have with them to ensure you’re achieving the outcomes you want?  How will you track and measure outcomes? What will you do with that data?

Finally, once you have your program strategies in place, you have to think about tactical execution. This is NOT in the weeds – this is not you executing. Rather, it’s being clear about which tactics to use. What staffing will you need? What curriculum will you need? What partnership contracts will you need? 

So as a leader, you have to have time away from putting out fires and facilitating staff meetings so that you can engage with each of these levels of thinking and work. 

You don’t want to spend too much time in any one space because, like I said, they build off of one another. If all you do is generative thinking, then you miss the ability to work with your team to map out the way forward and people feel lost.  Similarly, if everything you think about is at the tactical level – which policies we need, what our staffing model should look like, then people still feel lost because those tactical decisions are devoid of context.  

The struggle to strike a balance between the 3 unfortunately never goes away. 

So I want to highlight 3 strategies for bringing each of these modes of thinking and working into your life. 

The first is about how to create space for generative thinking. 

Again, this is the level of thinking where our purpose and mission live – where we’re able to think about the kind of organization we want to build, the kind of staff culture we care about, the next level of impact we want to have. 

My suggestion here is to have an annual personal retreat, or CEO Day. We plan board retreats and staff retreats to create space for value-based and generative work with our staff. Plan a half day or full day retreat for yourself. 

I did an entire episode about this called The Power of the CEO Day on November 1st. It’s like a mini-training on conducting your own CEO Day, and I’ve included it on the playlist! 

I also have a more in-depth toolkit inside the resource hub at

This is not a personal day. It’s not about getting a massage or sitting by a pool. Treat the day the same way you would a staff retreat. Identify your objective for the day and plan an agenda.  

The main difference is that this agenda is aimed not at helping your staff to bond or do strategic thinking and planning together. Rather, it’s about taking a step back as the leader of your organization and checking in about how you’re doing. 

Ok, strategy two is about how to bring in time for Strategic thinking – outside of say a strategic planning process. Carving out time for strategic thinking – planning, problem-solving – can be really tough. 

Here, I recommend hosting brain trusts for trusted advisors and stakeholders in your network. 

Generally speaking, a brain trust is a convening of well-informed advisors and experts who are brought together to advise you on a specific strategic challenge or set of issues.

The idea of bringing together a group of close advisors who have specialized skills or expertise is not new.  As a term of art, it’s most associated with FDR who pulled together a group of expert advisors during his presidency who played a key role in helping to shape his thinking around the New Deal.

For our purposes, a brain trust is a stylized meeting – aim for about 1.5 hours – that brings together advisors and experts to help you think through and strategize around a problem.

I did an episode walking through this called A Fun (& Powerful) Cultivation and Network Expansion Activity, on August 9th of last year. I talked about it as a powerful cultivation strategy – which it is. But it’s also a powerful way to provide dedicated strategic thinking space for you and your team. 

This is also in the playlist! I walk through what they are and how to set them up in the episode. I also include a braintrust toolkit, with a full implementation guide and model agendas, etc. inside the Resource Hub at  .

Finally, the third strategy I recommend – this one for engaged tactical thinking – is one of my favorite: the listening tour.  I used this strategy from year one of both of the organizations that I started, and I actually still do this in my current business. 

Its so simple and powerful! 

The basic idea here is to have 2-3 meetings, coffees every quarter with people who can help you learn to do something better.

Think of 3-4 things you want to know how to do or do better. When I first started doing listening tours, I wanted to learn about how to structure a volunteer-based program. Nuts and bolts – hours of training, where to recruit, how to terminate if they were awful. 

ID a few people who you think know the answer to your question. You’re going to reach out to those people and ask if they will have a 1-hour coffee with you about a specific organization question. 

A couple things to note — They do not have to be in your space — they can be in a different sector, at an organization that does completely different work. This is about expertise and experience – who are the people that know the answer to your question and can give you insight and expertise. Period.  You do not have to know them — this is a great way to build your network. 

Do this 3-4 times/ year.  Pick one question to start and set up 1-2 coffees. Then repeat 3-4 months later. That’s it.

This is a super simple strategy and really, really powerful. Some of the most impactful partnerships that I built in the early years of my org were through these listening tours. In addition to getting access to concrete, tactical insights in the short term, I’ve built professional relationships that have resulted in funding, that gave me access to people to invite to cultivation events, that introduced me to people in other sectors. 

One of my early coffees was with the head of ### for Blue State Digital – the incredible organization that helped to develop Obama’s online and social media outreach strategy for his first presidential campaign. I reached out to ask specific questions about how to think about cutting through the noise on social media to help teens actually be heard and have an impact on social issues. That coffee led to an amazing partnership and a brand new program for my organization.  

So those are 3 strategies I recommend – if you were to do 1 CEO, 2 brain trusts, and 3 listening tours — and actually get them on your calendar – just like tat you have a full year of planned strategies that will create space for you to come out of the fray and think about your organization as a whole entity.  

One last thing I’ll say is that there is no silver bullet. Making time to work on your organization will always be tough. But you gotta do it. Doing it doesn’t have to mean hours upon hours every week – you can use these simple strategies to integrate different modes and levels of thinking into your work throughout the year.  

Ok, so as a reminder, you can get the entire playlist with the mini0trainings on CEO Days and Brain Trusts at

You can get the CEO Day and Brain Trust toolkits inside the Resource Hub at 

Links Mentioned

Get Out Of The Weeds Playlist:

A Fun (& Powerful) Cultivation and Network Expansion Activity

The Power of The CEO Day

Nonprofit Resource Hub:

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