How to Include Your Team in Your Strategic Planning Process

There’s another way strategic planning is like sailing: You have to inspire your crew for the journey ahead. For tactical purposes, you tell your people where they’re going so they can take the right actions to get to the destination. But that’s not the only reason. When you help the team envision the end result, it keeps their energy and morale high, so they can tap into higher levels of effort and performance.


One of the first steps in getting a company aligned is sharing the company’s vision and strategy. Schedule an all-hands call to provide background and context on the company’s priorities. The most motivating leaders spend as much time talking about why the priorities have been chosen as what they are.


By fully explaining what the future looks like, your teammates will feel a deep responsibility for achieving it. What’s more, you’ll have a whole team of people independently channeling their creative thinking and unique expertise to achieve the end result as successfully as possible.


Imagine the difference between your employees simply focusing on the task that’s been assigned to them versus feeling a shared responsibility for creating the future. When your team understands the bigger picture, they can anticipate and troubleshoot things you never knew to think about. On top of that, their discretionary effort will shave off unproductivity and errors that affect your timeline and your bottom line.


Incidentally, all of this further amplifies the quality of your strategic planning, as well as how your team performs.  As CEO, you typically decide the vision with input from your leadership team and trusted advisors. But now your strategy can be informed by the insights and experience of your whole team. (Skip-level 1:1s are great for learning from your employees and testing ideas for your strategy).


In fast-growth companies, this virtuous cycle becomes essential to how the team operates. Leading to better results and a team that is emotionally connected to the company.





3 Key Questions for Annual Strategic Planning

Earlier, I shared my philosophy that strategic planning is a lot like sailing. When you’re under sail, conditions can change quickly. You frequently need to revise and refactor your plans along the way. 

In this case, instead of assessing the winds and weather, we use probing questions to dig into what’s enabling– and standing in the way of– your company achieving its most important priorities. Then we use those insights to confirm or adjust your plans. 

Successful founders use strategic planning–both annually and quarterly–to get to their vision as quickly and as profitably as possible. 

At each strategy session, you’ll look back on your progress, your challenges and other factors affecting what you’re trying to achieve. Then you’ll apply that knowledge to your upcoming plan. 

I always recommend quarterly strategy sessions, because a lot can change in three months for fast growth companies, and it enables us to pivot quickly. 

But it’s essential to take a top-level view at the end of the year as well; looking towards the full year ahead; a.k.a., the next big leg of the journey. 

In annual planning sessions, we ask three key questions: 


#1 Have we arrived at where we thought we’d be by this point?


Start by reviewing your company’s key metrics and goal plans. 

Did you achieve what you expected this year? If so, what people, processes, tools and other factors helped make that possible? If not, why not and what can you learn from it? 


#2 What adjustments do we need to make to stay on course? 


Take some time to reflect on your top priorities. 

Does your destination remain the same? Does it need to be adjusted now that you’re closer and have more information? What are your competitors doing and how might that change your direction? What changes or investments do you need to make to your people, processes and tools to stay on course?


#3 What are our new annual priorities? 


When you’ve arrived at the end of the next year, what does your destination look like? What have you achieved? What new features or products have you created? How much has your customer base grown? 

Once you’ve answered these questions, create a short, specific list of your top priorities for the year. This ensures that your team focuses their effort and energy on the most important outcomes.

Next, chunk your annual priorities into quarterly priorities to keep a clear line of sight. Then, cascade your annual priorities into a short list of team (or department-level) goals. Lastly, set individual goals for each team member that align to their team goals and the company’s top priorities. 

Next up: why and how to bring your people into your strategic planning process.

7 Strategies for Leading Your Company Through Tough Times

Every founder faces tough moments–it’s inevitable. It could be that your strategy isn’t getting the results you were desperately counting on. Or, new users and your bottom line are lagging. Perhaps your latest release is riddled with defects and even your most loyal customers are leaving you.

Or it could be that a global pandemic interrupts life as we all know it. COVID-19 is new, but unforeseen business and leadership challenges are not.

Without a doubt, these are times that test us. But when every day feels like you’re going into battle; those are the times that count the most.

When so much is expected of you and so many are counting on you, it can be exhausting and overwhelming. I’ve coached hundreds of leaders through their toughest times and I know you can get through this, too. Here are my top seven tips:

#1 Get Your Head Right

You can’t be there for your team if you haven’t taken care of yourself first–both mentally and physically. Taking time to recharge will make you exponentially more productive and present for the rest of the day.

How do you know if you need to reassess your habits? Watch out for warning signs like your daily run getting replaced by a few glasses of wine, or a new Diet Coke habit that takes the edge off the sleep you’re not getting.

Suggestions: Meditation has been a game-changer for me. Headspace is my personal favorite. (Yes, I swear the subscription is worth it, and no, I’m not a sponsor; I just love it). That’s not all: do something at least three to four times a week that makes you sweat and that’s easy for you to fit into your schedule (a run, a Peloton ride, an on-demand workout, etc). Block time in your calendar to hold yourself accountable.

#2 Watch Your Pace

You may feel like taking time for yourself is a luxury you can’t afford, or that your company can’t spare you for that hour. When your company is going through an intense or tough period, the pace can be addictive.

The harder you work; you lose perspective on the big picture. The longer it goes on, the less possible it feels to take time for yourself or your family, or to find balance. You don’t realize it in the moment, but that relentless pace undoubtedly results in diminished performance, decision-making, and how you “show up”.

Suggestions: During the most extreme circumstances (monthly churn is in a death spiral; you’re scrambling for your next round of funding; your app keeps crashing), this pace will be unavoidable. In which case, do the best you can to eat well, get enough rest, and power through.

However, if this has become your business as usual, acknowledge it for what it is and take steps to force yourself to rebalance. This includes putting Slack on Do Not Disturb and shutting your laptop at night. Spend time with people you love. Go out to dinner. Go for a walk. You will wake up with a fresh perspective and a better mindset.

#3 Manage Your Style Under Stress

Hopefully, you already know about your personal strengths and limitations. You may have gained this insight through a Founder Feedback process (a structured process where you get feedback from the people you work closest with), or from trusted mentors and teammates.

It’s human nature that, when we’re stressed out, our weaknesses are more prominent. For example, if you tend to have a quick temper on a normal day, you’re even more likely to have one when you’re stressed. The same goes if you tend to avoid conflict, or if you secretly think you’re the smartest person in the room, or if you’re overly critical of others, or whatever it is you’re personally working on. The things you’re normally challenged by will get amplified if you don’t actively and aggressively manage them.

Suggestions: To avoid your style going negative, take note of triggers and remove yourself from the situation. When you feel like your level of stress is causing you to lose perspective (which happens to the best of us), ask people you trust to be on the lookout for the warning signs. Lastly, remember that managing your mindset and pace will help you stave off negative styles.

#4 Communicate More, Not Less

There are so many reasons why leaders tend to communicate less during tough times. Maybe it doesn’t feel like there’s enough time in the day. Or you don’t feel like you have the emotional capacity to rally the team because your stress is at its peak. Maybe you just can’t bring yourself to pull the team together because you feel like you have nothing encouraging to say.

It will be one of the harder things you’ll have to do, but put aside those doubts and excuses, dig deep, and do it anyway–frequently. One of your most important jobs is to be present for your people. They need you to support, guide and encourage them, especially during uncertain times. The longer you wait, the more the anxiety will creep into your team and affect their morale, performance, and productivity.

If you don’t fill the communication vacuum, other people will create the message for you. Their message will almost always paint the darkest version of any situation.

Suggestions: Throughout the month, use a combo of communication mechanisms to connect with your teammates:

  • Send an informal note to the team.
  • Share a daily or weekly video with your personal thoughts and words of encouragement.
  • Share personal perspectives and get firsthand feedback at 1:1’s.
  • Communicate key messages and create alignment on all-hands calls.
  • Build connection, trust, and culture at theme-based all-team calls.

#5 Be Human

When you talk to your team, be yourself. Don’t be afraid to share how you’ve personally been affected by the tough times you’re going through. It’s OK to let people see the doubts and stress you’re facing.

For example, after 9/11, our leader who wasn’t known for her soft side unexpectedly broke down in tears in front of the whole team. In addition to managing the impacts of the company in crisis, she was concerned about her daughter who lived in Manhattan. Her team saw a side of her that she had previously kept from them.

Rather than seeing it as a sign of weakness, our understanding and appreciation for her as a person and a leader expanded significantly. This is what people mean when they say to be authentic and human: Be open with your feelings so your team can share the experience with you. There’s nothing that builds connection more than a leader who lets the team know that they’re going through it too.

Suggestions: Talk about the things that matter to you and how you’re being affected. Share examples and tell stories.

Though, to be clear: Don’t misconstrue authenticity to mean spontaneity. Have an idea of what you want to say ahead of time to prevent over-sharing or coming across as insensitive to your people’s challenges (which could be greater than yours). Turn your video on and let people see your body language in addition to hearing your words.

#6 Don’t Sugarcoat It

Don’t sugarcoat the challenges you’re up against. Humans have a keen sense for bullshit. The quickest way to destroy trust and credibility with your team is to massage the truth or avoid it altogether.

In most cases, your team will be able to handle reality, and it’ll help them know how to direct their energy toward the things that are most critical to your company in that moment. They’re the ones who will pull the company through the challenge you’re facing. Being transparent and telling the truth builds the deepest kind of loyalty.

Suggestions: Your team will be hanging onto every word, so be deliberate about how and what you say. As above, spontaneity is not your friend at these times. Decide on the key messages you want to share with the team. Practice ahead of time if you’re nervous. If you’re worried about what your facial expression and body language might convey, video yourself as you practice.

#7 Give Your Team Hope

When things may seem uncertain, and in some cases even dire, there’s always a reason to be optimistic. Remind your team about what’s uniquely awesome about your company. It’s those things that will give them hope and inspire you and them to dig even deeper. Let them know that you’ll get through it together.

Suggestions: Grab a quiet moment and think back to the highest points with your team and your company. What made you great then? What still applies now? Your Core Values are a great place for inspiration.

This tough time will pass, but it won’t be the last one you face. Reflect on what you can take from the experience to make you and your company stronger.  Every day we have the ability to learn, evolve, get better. You will get through this and emerge a stronger person and leader for it.

Get Back in Control: of your time, your team and your customers

Office environment strategy

Last week, I wrapped up the Assessment phase with a founder and his leadership team. This is where we go deep and inventory everything the company has that relates to People and Culture, including surveys, interviews and a detailed content bank.

It’s a way to take complete stock into a company’s competitive strengths and opportunities related to their people and culture so founders can get back in control of their time, their work and their team’s performance.

Among other insights from the assessment, I was really impressed to see how many of his people felt deeply connected to their customers. And this is very good, for many reasons.

Because here’s the thing. Your company is your people.

Yeah, I know that’s not grammatically correct, but stick with me for a second. 🙂

I’m not talking about the fact that without your people, you wouldn’t have a product to sell or anyone to support it (which is obvious). What I mean is, your customers are buying your people.

Unless you are on the very cutting edge of the industry and no one has created what you are selling, then chances are there are a couple- or many- companies competing for the same share of the market. What differentiates you from your competitors is often not what you’re selling, but how you’re creating your niche in the market.

With options in front of them, customers have the luxury of choosing not just on features and convenience, but on whether or not they believe in you as a company.

When your customers choose you, they’re saying that they believe on a deeper level in your strategy and your vision and how that’s going to guide the continuous improvement of your product.

And who embodies all of this, and executes on your vision to make that future a reality?

Your people.

This is why it’s so important that you treat your people like the biggest (and most expensive) asset that you have.

Because that is exactly what they are.

Team talking about strategy

And yet, many early-stage entrepreneurs pay far more attention to other things when they’re running their business. Without a doubt, there are many capabilities that are important to invest in like customer onboarding and market positioning.

But if your strategy for running your team equates to delegating the responsibility to somebody else with a passion for it, or planning a fun-filled retreat without much strategic substance, or if your admin has evolved into your Head of People, then you are most likely missing some very important opportunities to get your most expensive asset aligned to what matters most.

So how do you get your people to be the living, breathing embodiment of your culture? How do you get your customers to buy you?

1. Know Yourself.

  • Before you can convince a customer that you’re unique, you need to know what that is. Start with your vision. When you daydream about the future of your company, what does it look like? What are you doing? What difference are you making in the world? Have you created something that no one has thought of yet? Are you solving a problem in a totally new way? What does the future look like?
  • Declare your Core Values. What are the beliefs that are intrinsic, fundamental to the way you and your company behave and operate? These aren’t good or bad characteristics, and they’re not aspirational. They simply are. They’re the things that your team goes back to when they’re proactively making decisions without you, that you use when you need to make trade-off decisions about everything from product features to your employee benefits. They’re a guide for how you hire and reward your people, and for how you ensure your teammates are a good cultural fit. Know yourself and declare it unapologetically to your people and your customers.

2. Know what you need to achieve in the next 12 months – and in the next quarter.

  • Working with your leadership team, think across every workstream you have. Where do you want these things to be in 12 months?
  • Decide on your top three priorities. It’s important to keep this list short. In order to execute well, your team needs to be aligned and focused on the narrowest number of things to ensure the greatest chance of success. Avoid the temptation of expanding to more than five as it will significantly reduce your ability to accomplish any of them well.
  • Once you do this for the company, each of your leaders should do the same for their specific area of accountability.
  • Now do the same thing for the upcoming quarter. Chunking it out into quarters ensures a constant focus and makes your goals feel more manageable to achieve

3. Establish meeting routines that support it.

  • Meetings can be a double-edged sword. Too many of them and they’ll kill productivity. Not enough decisions coming out of them and they’ll kill morale.
  •  I’ll get into meeting routines in detail in another post. For now, keep in mind that the right ones, used deliberately and consistently, will make all the difference in keeping your people aligned and your business growing.

4. Communicate communicate communicate.

  • Once you’ve gotten to this point, your next priority is to communicate these things thoroughly, regularly and consistently. All the work you put into the other stuff will be worthless if the only people who know about them is you and your leadership team.
  • This is the most crucial step if you want your teammates to deliver on the unique value proposition that you’ve created. It’s where a Core Value like “Keep it Simple” comes to life and becomes the decision criteria for your product roadmap, or the key message for your Customer Support team when they’re trying to win over new customers. The more you can connect your people to your strategy, vision, Core Values, and key priorities, the more they will deliver that value to your customers. Communicate this stuff many times, in many different ways. Stories are an incredibly powerful way to make these connections.
  • In addition to the value this creates for your company and your customers, don’t underestimate how important this stuff is for your people, especially your highest performers. Like your customers, your teammates need to be emotionally connected to the bigger picture to give the kind of discretionary effort that leads to exceptional business results.

If a business is really thriving, founders will naturally reach the point where trusting their “gut” reaches its limit and inefficiency and misalignment begin to creep into their business.

The good news is that this is a totally normal stage for fast-growing companies. The bad news is that if left unchecked, you will lose control over your time, your work and your team’s performance. And your ability to get your customers to buy your unique value proposition will be seriously affected.

Instead of pretending that your company is still the same as it was when you were a seedling of a startup,  embrace that it’s changing in necessary ways to get ready for even greater things to come.

Don’t give someone else on your team the responsibility to make this shift. Only you can own it. And when you’re deliberate about executing on it, you’ll be the first to see how much better your team performs and the profits that go along with it.

So you can get back to the things you most love to do.