The difference between good startups and great startups: Planning and Execution

The difference between good startups and great startups: Planning and Execution

Welcome to Forge Ahead!

The Blog for Ambitious Startup Founders

From avoiding founder overwhelm to how to improve your investor readiness, and much, much more!

The difference between good startups and great startups: Planning and Execution

When you are building a startup, it can feel like there are never enough hours in the day to get to everything you feel you have on  your plate.  This sense of overwhelm means that some things fall through the cracks. For many founders, one common casualty is making time to review their strategies and update their operational plans .

Lots of founders make time to create a business plan or think about their strategies and goals when they are preparing their pitch deck.  But many see business plans and pitch decks as something that you create for other people. More than that, they see them as things that you do once as a special project.

The truth is that planning and execution are the lifeblood of startups, and making time to review and update your plan is crucial.  Your business plan should not be a static document. It should be something that you share with your organization and  use actively to build and execute your vision.

You never hear anyone say that investors invest in founders that can come up with great strategies, or founders that have lofty goals. Instead, you hear that investors bet on founders that can execute.  And execution starts with a plan.

It may seem like common sense, but I speak with a lot of founders that don’t have plans they can use to manage the business. They have strategies, like their “go to market” strategy, or their “product development” strategy.  And they have goals, like “we’ll increase revenues this year by X%” or “we’ll expand internationally in 2021”.  But you can’t execute these strategies or goals without a plan.

So what are the required ingredients of a good plan?  Here’s my list:

  • Tactics and actions
  • Deadlines/schedules
  • Progress metrics

There are lots of YouTube videos that include a lot more things, but I want to keep this simple. If your plan includes these elements, you are already doing better than a lot of founders.  I’ll elaborate a little on my 3 requirements.

Tactics and actions

The biggest problem with strategies and goals alone is that they don’t tell you what you need to do day-to-day. To achieve your goals you need the methodical application of tactics and actions.  That can include things like:

  • Contact 40 customer prospects per week
  • Create weekly content targeted to our target market about [insert problem]
  • Negotiate volume pricing for …
  • Review website analytics and launch new A/B tests monthly
  • Develop an email campaign to reactivate inactive customers
  • Poll existing customers on service or satisfaction levels

For your business, what are the daily, weekly, and quarterly activities that you, or members of your team, can do to produce the result you want?  Do you have a list of those activities? Do you know who owns each of them?  Are you tracking that they are being done and do you have a way to track their effectiveness?


Deadlines and schedules are usually the second big gap in startup plans.  Annual goals are a lot like the term paper assignment you got at the beginning of the year. There is no urgency to work on it.  With startups, you need to create urgency around your strategy. That means mapping out a timeline and due dates for your actions and tactics. 

You should break annual goals down into shorter-term milestones, like monthly or weekly.  Some of the actions and tactics will be one-offs, and some will have to be routines. What’s important here, especially as your team grows, is that these actions are coordinated, and that can only happen when you schedule them. 

I see founders who are lax about due dates and deadlines, but you need to treat meeting deadlines as an organizational discipline.  If you are lax at the beginning, that will become part of your culture. As you grow, the organization will be lax as well. And if you make promises to customers and don’t keep your promises as an organization, you won’t be in business long.

Create an organizational culture where deadlines and due dates matter.  It’s difficult to change the discipline of a culture once it starts to set. Setting and meeting deadlines also helps your team coordinate their efforts. CEOs that make and keep promises about what they are going to do raise money MUCH easier than those that don’t!

Progress metrics

I mentioned that goals don’t inherently have urgency, like that term paper. Setting near-term deadlines and incremental milestones helps you create a sense of urgency and manage workflow. It also gives you an objective way to track and measure your progress, make sure that you are on schedule, and let you see if the tactics that you are using are effective. 

The one thing you need to know about plans is “They change”. Mike Tyson famously said, “Everyone has a plan until they get punched in the face”.  Your progress metrics are your way of quickly seeing what actions are working and which are not. If you don’t have progress metrics in place, you risk wasting a ton of time and money on ineffective actions. Progress metrics also gives you the ability to identify problems, adjust your plan, and get back on course.

When something isn’t working, be sure to ask “why”.  Is the tactic flawed? Is the execution flawed? Are we hitting the right audience? Whatever the reasons, take the opportunity to learn from your “why” and adopt new tactics.  Then rinse and repeat.

When you are creating your company roadmap/plan…

  • Start with developing clear and achievable Goals/Objectives
  • Make a comprehensive list of the activities that will be needed to meet those goals
  • Break the goals down into quarterly and monthly goals and weekly deliverables
  • Identify the metrics you’ll need to see to know if things are working as planned
  • Make sure all activities and deadlines have someone who is responsible for them
  • Track, review, and analyze your results on a regular basis
  • Update and adjust your plan as needed

As soon as the organization is more than just you, you will need to have a way to give your team visibility into the tasks, deadlines, and key metrics.  You don’t have to use something sophisticated or expensive. Many founders start with Google Sheets or anything cloud-based that multiple users can see and update. If you wanted something a little more sophisticated, you can easily build project tracking sheets in Airtable or Notion. And lots of project management software, like Asana or Clickup, have free versions to help you get started.

Go forth and execute

Hopefully, you are already doing most of the things in this post.  If not, here’s your checklist to supercharge your company’s execution:

  • Make the time to review and update your plans regularly. Adjust based on what’s working and what’s not. Also consider updates based on: changes in the marketplace; feedback from your customers; and new opportunities that may have popped up.
  • Consider your plans to be fluid and adaptable and visible to your entire team
  • Create expectations for all of your activities.  Track the results early so that you know when to adjust
  • Have an individual responsible for critical tactics, and for keeping activities on schedule.  Let everyone know how their project fits into the success of the company
  • Hold people accountable to deadlines and lead by meeting your personal deadlines

I hope this helps. Go be epic.

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The Best and Worst thing about being a Founder

The Best and Worst thing about being a Founder

Welcome to Forge Ahead!

The Blog for Ambitious Startup Founders

From avoiding founder overwhelm to how to improve your investor readiness, and much, much more!

The Best and Worst thing about being a Founder

In my coaching practice, I run across common questions and themes.  Some of the themes revolve around the question of why being a founder seems way more difficult than you expected.  And while the tech media might make it look like every founder was an overnight success, I want to make sure you know that most of them felt like they were in over their heads for at least a moment.  This post is about one of my favorite reasons why this stuff is just plain HARD!

The best/worst thing about being a founder

Being a startup founder is harder in reality than most people think before they get started.  Some founders are drawn to one of the best parts of being a founder: not having a boss.  The funny thing is that for some founders, not having a boss is also one of the worst things about being a founder.

Let’s face it. Having a boss makes things simple.  Bosses are sort of the Google Maps of work. They tell you what you need to do and when you need to do it. They even tell you the destination that you should enter into Maps.  Sometimes, Maps will give you options on how to get to your destination and will even tell you the difference in the routes (usually in relative time), so that you have a feeling of choice.  But ultimately, all roads lead to the same destination: the one your boss gave you to begin with.

If you arrive at your destination and it turns out to be the wrong destination, that’s not your fault.  Your boss had the responsibility of deciding where you should go. Your responsibility was to get there to the best of your abilities. 

Was your boss doing you a favor?

Bosses provide all sorts of wonderful things that you might never have appreciated.  For example, they often give you deadlines and due dates.  I know what you’re thinking: “deadlines and due dates are wonderful?”  Now that you are a founder, you tell me.  When I work with founders, many of them struggle with two things:  They struggle with setting deadlines and due dates, and then they struggle with staying on schedule once they’ve created them.

It turns out that having someone else hold you accountable to deadlines is often way easier than holding yourself accountable.  Maybe we’ve been trained by those term papers that always had a deadline that some of us barely made.  But when there isn’t anyone to hold us accountable, deadlines often “slip”. That voice in your head says “It’s only a few days…”.

Another “gift” from bosses is prioritization.  What you don’t often realize when you have a boss is that there may be 100 things that you need to get done over the course of the year.  You don’t realize it because your boss is usually the one that decides what you should be working on right now. They’re prioritizing for you. They are looking at everything you could be doing and giving you the filtered list of what you should be doing at any given time.

Too much choice can be overwhelming

One of the last and biggest gifts that you get from your boss are “lane lines”.  Your boss gives you a limited scope of responsibility.  For example, you are responsible for marketing a particular product line, or selling to particular clients, or managing certain people.  When you have a boss, you might crave more. More power, more responsibility, more scope.  As a founder, you now understand the saying: “Be careful what you wish for”.

In summary, bosses:

  • Tell you what to do
  • Tell you what the destination is
  • Give you deadlines
  • Limit your scope

So is having a boss better than being a founder?

Not necessarily.  But having a boss and being the boss are two very different things. You should expect that making that transition can be challenging.  For example, without a boss, we have to take on a host of new decisions that we formerly took for granted.  And those decisions carry the weight of success or failure with them.

For starters, you have to decide: 

  • What the company is going to make…
  • Who the company is going to serve…
  • How the company is going to make money…
  • How it’s going to create its product/service…
  • And a thousand other details that will be the foundations of your success!

These decisions, in aggregate, will become the “destination” you need to enter into Maps.

But wait! There’s more…

Once you decide the destination, you have to essentially build the vehicle to get there.  And this doesn’t mean that you get a box of vehicle parts labeled with instructions like something Ikea would do if they made cars. It means deciding what vehicle you want, determining what parts you need, and how you need to assemble them.  Think “random Ikea parts with no instruction manual”.

Next, you need to set deadlines for this heap of uncertainty.  The first version of the vehicle will be ready by “x” and the destination will be set by “y”.  We’ll assemble a crew in the next 30 days and we’ll get the money for the trip in the next 90 days.

Without a boss, it’s up to you to decide what tasks and projects have priority. After all, you have limited time, limited personnel, limited money, and an unlimited list of things you “could” do.  So you have to determine where your time and resources can be most effectively spent to help you meet your deadlines and get to your destination!

And last but not least, as the founder, you are responsible for all of it. Yikes!  And did I forget to mention that when you have a boss, you don’t have to figure out how to pay for it all or have to find investors?

So if you are wondering why starting a company has seemed harder than you thought, maybe this will clarify things.  You should also know that you are not the only founder feeling like this founder gig is tough.  But, as the saying goes: if it were easy, everyone would do it.

So how do you make it easier? 

Don’t try to do it all by yourself. 

  • Recruit a strong team that can help you figure out the destination and that you don’t need to micromanage  
  • Look for advisors, mentors, and coaches
  • Speak with other founders and find your brain trust
  • Find the types of investors that can help you navigate the decisions, not just give you money
  • Remember that you are going to get a lot of decisions wrong. That’s part of the process.
  • Commit to learning from your wins and losses everyday

Being a founder is tough. It’s an emotional rollercoaster. It’s also very fulfilling when you get it right.  Acknowledge that it’s difficult, make mistakes, and then get it done.  If you find yourself struggling with any of these things, let me know, I’m happy to help.



Creating a strong value proposition

Creating a strong value proposition

Who values your Value Proposition?

A value proposition tells people why they would buy your product, yet a lot of startups have value propositions that are met with little, if any, enthusiasm.  This post should help you look critically at your value prop and see if it has the right ingredients.

Each year, CB Insights publishes a research brief called “The Top 20 Reasons Startups Fail”.  And each year, the #1 reason is “No market need” (42%). You  might wonder how it is that there is no market need for products and services that are clearly better than legacy products, faster than legacy products, and cheaper than legacy products?

Generally speaking, the answer is: because the product wasn’t created with a real understanding of a particular customer.  That may sound like an oversimplification, but hear me out.

A big part of my coaching work with founders is about helping them see what’s holding them back. And because founder coaching is about both the founder and the company, I help them surface what is holding their company back as well.  I recently wrote a blog article about how Founder Bias was one of the things that held companies back.  In that article, I spoke about why customers might not be interested in your product.  Your value proposition, when done correctly, focuses on why they would be interested.

I started this piece talking about the necessary ingredients of value props.  If you Google: “definition of a value proposition”, you get a pretty wide range of answers. Some of the definitions that I like the most are:

  • “A value proposition refers to the value a company promises to deliver to customers should they choose to buy their product.” Investopedia
  • “Your value proposition should describe; how your product or service solves/improves problems, what benefits customers can expect, and why customers should buy from you over your competitors.” Impact
  • “Value Propositions are the products and services that create value for a specific Customer Segment. They do so by solving a customer problem or satisfying a customer need.” E-Commerce Digest

I like those particular definitions because they include clues to the “necessary ingredients” that I mentioned earlier as being part of great value propositions.  Each of these definitions include the words “value” and “customers”. I see a ton of startups that either don’t understand “value” or don’t understand their customers. Value is what people pay for, not features.  Customers are the folks that make the purchase decision.

Defining “Value”

The first thing you need to understand is that value, like beauty, is subjective.  Two people can be presented with the same set of product benefits and have two wildly different perceptions of the value of a product.  Among other things that means that you can’t generally create a product or service that has “universal appeal” and by extension, universal value.  

The second thing to know is that generic benefits don’t necessarily correlate to a person’s perception of value.  Value is a personal calculation. It’s a net of a lot of different things and that calculation is different for different people.  One’s perception of value is a primary driver of what someone would be willing to pay for something. And what people are willing to pay for your product or service is a critical component of your business model.

The calculation that I mentioned isn’t always numeric, it’s quick and intuitive.  “Will this product add more value for me than the cost of adopting the product?” “Does this product improve my life in a meaningful way?” “How often will I use this?”

So if value is based on “personal” perception and an individual’s specific net calculation, you can see that a great value proposition has to start with a specific set of individuals in mind: your target audience.  Your value prop should start with a strong idea about who needs your product. So when we talk about the “pain point” or the “problem”, you need to have given some thought to who exactly has the problem you are seeking to solve.  This might seem obvious, but you might be surprised how many founders assume too broad a target audience.

  • Good startups start with a thesis about who would really value their product.  
  • Better startups validate that their original guess was correct. 
  • Great startups dig deep into the motivations and worldviews of this set of potential customers to understand what they would see as valuable.

What about not-good startups?  Those startups start with a product.  They get wrapped up in the bells and whistles, the features and capabilities, and the “cool factor”.  Bad startups think about the customer last. They build the tool and then go around looking for people that might want the tool.  They work hard at trying to convince or persuade potential customers that their product has value. If you need to do much persuading that your product has value, your product might not have the value you think it does, or you are trying to sell to the wrong person.

As a startup, you should always start with a strong need and knowing exactly who has that need.  That way, you don’t have to persuade them that they need a solution, you just need to let them know why you should be the solution they select.

Theorize your initial ideal customer

So how do you create an effective value proposition?  Start by thinking about a specific group of people that are experiencing a certain use case and would love to improve their situation by a meaningful amount. In other words, find a group of people who care about a current use case outcome and are ready to make a change.  

I emphasize “change” because that often gets missed by founders.  The fact is that adopting your product requires a change of some sort. Humans don’t especially like change.  We’re creatures of habit. We change when we think that the personal value of the improved outcome is worth the risk or the switching pain.

Personal value is different from generic value.  For example, if I made a “better” running shoe, the word better doesn’t mean the same thing to all people.  To some, better means more comfortable. To others, it might mean more breathable. To still others, it might mean that it helps you run faster.  So your “better” shoe might not be better to me. You need to start with a group that aligns with your idea of “better.” 

The value to any customer is going to be outcome focused.  For example, the product will get them to their destination quicker, or make it easy to coordinate all of the transportation and housing for a vacation, or help them get investor funding in half the time.  The value won’t be centered around features or the mechanics. 

Don’t stress about whether you will initially guess right about who the best customer is.  A lot of startups either misidentify the target audience or the problem, or both. If you pay attention and iterate, there should be time to adjust.  The key here is at least having a starting customer in mind that you can build assumptions for and that you and do customer development interviews with. 

Don’t be married to your starting assumptions

Your value proposition is likely to evolve over time. It could even evolve the moment you start having conversations with your target customers or seeing how they interact with your product.  What matters is that you start with a theory and validate your assumptions as quickly as possible. Your initial thinking might be wrong about the ideal customer, wrong about the perceived value, or both. If customers are not as excited as you expected about your product, it’s likely due to a mismatch in their perception of  value and yours.  

Also keep in mind that, in addition to showing value to your target clients, the best value propositions include strong value relative to other products and solutions.  After all, the target buyer has 3 choices:

  • Stick with their current solution
  • Switch to someone else’s product
  • Switch to your product

Lastly, be clear and simple.  Although your value proposition will be targeted to a particular audience, anyone should be able to understand it.  Use short, simple sentences. Don’t use big words or jargon or try to make it sound overly professional. And don’t exaggerate or use hyperbole.  I see startups that make unsupported claims or overstate their value. As a startup, it is vital that you deliver the value you promise.

Having a strong value proposition has lots of obvious benefits, but it can also serve to make sure that your entire company is focused on exactly how you deliver value to your customers.  A well crafted value proposition will impact all of the departments in your company and help you to establish your place in the market. 


A great value proposition will:

  • State clearly what you do
  • Be created with a particular user in mind and be based on what they would see as valuable
  • Be short and simple. Value propositions don’t include jargon or buzzwords.
  • Show not just absolute value, but show value relative to other options in the market
  • Be a work in progress that will evolve as your users, your market, and your competitors evolve


To finish, I wanted to show 10 company value props done right.  Enjoy!

Slack: Slack gives your team the power and alignment you need to do your best work.

AirBNB: Top rated, unique experiences around the world

Uber (for drivers): Get in the driver’s seat and get paid

Uber (for riders): Tap the app, gt a ride

Unbounce: Create custom landing pages with Unbounce that convert more visitors than any website—no coding required.

Stripe: Stripe is the best software platform for running an internet business. We handle billions of dollars every year for forward-thinking businesses around the world.

Zapier: Easy automation for busy people. Zapier moves info between your web apps automatically, so you can focus on your most important work.

Spotify: Music for everyone. Millions of songs. No credit card needed.

Asana: Asana is the work management platform teams use to stay focused on the goals, projects, and daily tasks that grow business.

Dollar Shave Club (clearly evolved):  A top-shelf grooming routine. Personalized for you.

MailChimp: Our all‑in‑one Marketing Platform gives you the tools to find the right customers, build your audience, and bring your brand to life.

Founder Bias (Blindness) is holding back your startup

Founder Bias (Blindness) is holding back your startup

When you work with a variety of founders, a number of patterns emerge.  In my work coaching early stage founders, one of the most common issues I see is Founder Bias or Founder Blindness. They are variations on a theme, but both, if not addressed, can be fatal for a startup.

Being a startup founder is hard. I say that in a lot of my blog posts because it’s hard in a variety of ways, including the sense of isolation, imposter syndrome, navigating amid uncertainty, the pressure of making things work, etc.  For this post I want to talk about how founders have to walk a fine line between between being enthusiastically in love with their idea and being able to see past their own blind spots.

Have you ever had a conversation with a founder where they are frustrated that people “just don’t get it”?  “It” being the brilliance of how their product will change lives. Or what about conversations where the founder is convinced that they “just haven’t found their audience yet” (which might be true)?  How about the conversation where they have all sorts of the metrics that show things like anemic conversions or weak engagement, but they just want to give it “more time”?

By themselves, these are not horrible things for a founder to say.  But at some point, if the founder isn’t making changes to address these things because “eventually things will take off”, then that’s either founder bias or founder blindness rearing its ugly head.

How are Founder Bias and Founder Blindness different?

For the purposes of this piece, here’s the difference between “bias” and “blindness”. Bias is when a founder is inclined to believe something more than the data that they have would support.  They see what they want to see in the data or more often, don’t feel the need to research data because they feel that they already know the answer. If you show a founder with founder bias real data that contradicts their bias, they are sometimes open minded enough to consider that their bias might be unwarranted.

When a founder has founder “blindness”, they’re “true believers”.  They know that they are Correct (with a capital “C”). Almost no amount of data can convince them that they need to adopt a new strategy.  Unless the founder is right and never needs to adjust course, blindness is terminal for a company for a lot of reasons. The most obvious reason is that investors can spot founder blindness most of the time and will steer clear.  No one wants to invest in a founder that isn’t open to course corrections when needed.

On the other side some founders aren’t so much biased or blind, they just don’t have the instinctive empathy for their customers and don’t know why things are not working as planned.

There is an exercise that I usually have my clients do, that can help them see past their blind spots.  The exercise is designed to pull the founder outside of “invented here” mode and help them imagine “why” there is a gap between their expectations and reality.  The exercise is “Why Not?”.

To do the exercise, a founder should have an open mind and be willing to let go of the things that they know about themselves, about their company, about the product, and about the magnitude of the problem they are addressing. It’s an even more effective exercise if it’s done with a number of people involved. Maybe as a group exercise for the founding team.  Even better if it includes people who are not emotionally invested in the product at all, like friends of the founding team. I’ve done this exercise with many of my coaching clients if they don’t want to make it a team project.

The rules of the exercise are simple.  

First you need to create a persona or personas for someone who fits the demographic and psychographic description of someone you would expect to be an “early adopter”.  This person should have the capability to pay for the product and the authority to purchase or recommend the product. They should be someone who regularly encounters the use case where your product adds value.  In short, they fit your target, have the problem, and have no limitations in being able to become your customer.

The persona should be considered to be sane and intelligent.  They make sound judgments for good reasons. In other words they are rational and are able to grasp the information “that you share with them”.  I put that last part in quotes intentionally and will explain its importance in a moment. The key to this part is that this person should be as close to a slam dunk early adopter as you can imagine.

Now comes the tricky part.  Now you have to imagine that you pitched or marketed your product to this person and they decided “thank you, but no thank you.”  This is where the hard part begins. Based on your thinking, this person should have been a “yes”. In reality, they were a “no”. Why?

Why wouldn’t they buy from you?

It’s time to make a list. But before you do, you need to remember two things.  The first is that this person does not share your thinking.  

  • They don’t know what you know. 
  • They don’t think like you. 
  • To them, you are a stranger. A startup. Someone without a deep performance history. 
  • They don’t know how smart you and your team are. 
  • They don’t care that you’ve raised money or graduated from YC.  
  • They don’t know the research that you read and have not seen the spreadsheets you created.  
  • It doesn’t matter to them how long it took you to develop the prototype 

The second thing is to recognize that what they do know comes from two places.  They know what they knew before you encountered them, and they know the information that you shared with them (mentioned earlier).  

The information they had before includes:

  • Their personal experience with the pain point/use case that you are solving
  • Their history with the legacy product that they currently use for that use case
  • Their awareness of other current options for that use case
  • How the decision to purchase your product might impact them personally
  • Anything they may have heard about you from other people
  • Their perceptions and worldview 

The information you shared with them starts with your initial marketing message.  It’s pretty limited. If the headline isn’t compelling, don’t assume that they scrolled to the bottom of your landing page. If the landing page isn’t engaging, don’t assume they know what you would tell them on a phone call (since they may never make that call).  So in short, they may not have known much about you before you reached them with your marketing, and what you shared with them might be limited.

Time for some Persona Empathy

So now you make the list based on everything above.  The list is a list of the reasons why this perfectly sane person, with no limitations on becoming a customer, decided to pass.  To get you started, here are some common “reasons to say no” that might have a place on your list:

  • They don’t believe your claim/assertion on the product’s impact/effectiveness (you don’t have social proof or they don’t believe your social proof)
  • They are worried that you won’t stay in business and they’ll be left with an unsupported product
  • The switching cost from their legacy system to yours is too high
  • The learning curve or change in workflow isn’t worth the impact they perceive
  • They don’t trust you with their information (especially with products that require sensitive information)
  • They don’t think that their legacy product is as bad as you think it is
  • They don’t perceive the benefits of your product to be as big as you do
  • They don’t fully understand what your product does
  • They don’t have the need you think they do. At least not at the magnitude you think
  • They may see your product as a risky one to switch to (the purchase could affect how their judgment is viewed by others)
  • You get the idea. Your list will vary…

Be honest and really brainstorm the possible reasons.  When you’re finished with your list, go through each and ask yourself which ones you can and should try to address.  Keeping in mind that your product isn’t for everyone, ask yourself if anything on the list narrows your thinking on the definition of your early target market.

So far, this exercise has provided something useful for all of my clients.  At a minimum, this will give you some additional customer insights or increased empathy. At its best, it will help you address invisible roadblocks that can materially dampen your traction.  In either event, if you block some time and take this seriously, I promise it will be worth the effort.

4 storytelling tips to boost your startup success

4 storytelling tips to boost your startup success

I recently gave a presentation at GSVLabs on Effective Storytelling for Startups (a recording of the workshop is here). GSV Labs is an accelerator with offices in Silicon Valley and Boston and works with early stage founders to help them improve their odds of success.

The first part of the workshop was partially about redefining storytelling as something we do with practically everything we say and do.  The clothes we wear, the words we use, our body language, the cars we drive, our tendencies to exaggerate, etc. In other words, we aren’t just telling stories in board meetings, at investor pitches, in our advertising, or when setting company culture. We are telling stories all the time.

What most people don’t take advantage of is their ability to manage the narrative. That’s partially because they don’t recognize the amount that they’re telling stories.  It’s important to note that the stories you tell in aggregate form your “personal brand”. The stories you tell about your company create your corporate brand. And the combination of those two brands have a huge impact on things like: 

  • Your ability to raise investment capital
  • You ability to recruit great people
  • Your ability to form strategic partnerships

During the presentation I spoke about how you can instantly improve the quality and effectiveness of communications with a few storytelling tips.  At the end of the presentation, someone asked what I thought was the most important part of great storytelling. And while there are lots of videos about storytelling that focus on how you “tell” a story, I realized that I thought the most important parts of storytelling happened BEFORE you actually tell the story.

When I’m coaching founders, I encourage them to consider a few things when creating a story (pitch decks, presentation, meeting, etc.).   My top 4 pre-story considerations are:

  • Who is your story for?
  • What emotions do you want people to feel?
  • What do you want people to take away?
  • How can you help them see what you see?

I’m surprised at how often people don’t start with the impact of a story when crafting one.  So I thought I’d write a quick piece to let you know how these things help.

Who is your story for?

Most stories are not universal. Stories affect different people in different ways.  Have you ever gone to the movies with a friend and discovered that while you loved the movie, they hated it?  Or can you imagine how commercials for a fast food burger joint are received very differently by a vegan versus a fast food lover?  People hear your stories through different filters and mindsets. If you know what some of those filters are before you tell a story, it gives you the opportunity to decide whether the story is right for that audience as is, might be right for them with some adjustment, or just isn’t right for them at all.

Let’s use a fundraising pitch as an example. I sometimes see founders who are are at the seed stage trying to tell their story to Series A investors.  It should be easy to see that this is not the right story to tell to this audience. And yet people try.  

Another version might be someone that is pitching the right type and stage investor, but telling them the same story they use in their consumer advertising.  Investors and customers have completely different concerns and motivations. In that instance, the founder should tell the “investor story”, which addresses things about the business prospects, not focused on the product benefits.  

A third variation would be someone trying to pitch an investor on a product that  focuses on a use case that the investor has no direct experience with and little empathy for.  The question there is whether the founder can help the investor relate to the product or market be relating it to something that the investor is already familiar with.  That’s why so many founders include analogies in their pitch. It’s an attempt to help the audience connect with something unfamiliar by comparing it to something familiar  Another tactic is to use a case study and give the investor the perspective of a customer.

If your audience doesn’t relate to, care about, or understand your story, you won’t get the reaction you want.  Craft a story that’s right for the audience you are telling your story to. I’m not suggesting that you lie or change facts, but rather that you be thoughtful about who would appreciate, understand, and be positively impacted by the words you choose to use and the picture those words create..

What emotions do you want people to feel?

When I say “positively impacted” in the section above, I mean a positive from the standpoint of the “hoped for” impact.  Good stories can create an emotional response, enhance a pre-existing emotional state, or have no emotional impact at all.  The question to consider in this case would be: what emotional responses are you hoping for? 

In the case of a pitch presentation, you likely want the audience to feel a number of things.  You’d want them to feel:

  • Confidence in you as a founder
  • Curiosity in wanting to learn more about what you do
  • A sense of exhilaration about something new and exciting
  • Belief that this is a strong potential investment opportunity

These may seem obvious, but when I am working with founders I see a lot of pitches that don’t do enough to try and create an emotional impact.  Instead they’re focused on just presenting facts and figures. Large market numbers might be a good start in creating some good emotions, but if they are not the right numbers, the response you get might now be the one you want..

If your story is the story of your brand, what emotion or feeling do you want that brand to evoke? Volvo makes you think of safety. Tesla is sexy. What do you want your personal or company brand to make people think of?  Should they be confident that you do what you say? Worried that you don’t care about certain things that are important to them? Thrilled that your corporate values seem to align with their personal values?

I know I’m using feelings and emotions as the same thing here.  And while they aren’t the same, they are intertwined. How do you want your stories to make people feel? With early stage founders, if your brand doesn’t suggest confidence (not cockiness), investors aren’t likely to feel confident in your potential for success.

What do you want people to take away?

Take aways are another thing. What do you want people to remember from your presentation? What would you like them to do or want to do?  This is important because if you can decide what you want people to take away from your story, it becomes easy to look at your story, presentation, or pitch and decide what information in the story doesn’t support your takeaway goal.

With some of my Founder Coaching clients, one of the big issues they start with is not having enough time to cram all of the things they want to say into the amount of time that they have to say it.  They want to cram 30 minutes of story into a 10 minute window. More often than not, when we start looking at the story and look at the intended takeaways, it’s easy to see that a lot of the story content has nothing to do with the takeaways.  

The issue with that is that the audience’s brains have limited storage capacity.  Generally speaking, they will only remember a fraction of what you include in your story.  If you dilute your story with a lot of words that don’t support your intended takeaway, there is a good chance that your takeaways will get muted.  Think about a glass of your favorite drink (pick something other than water). That drink is your story with a focused goal of takeaways and emotional responses. Now imagine that each additional thing you add to the presentation is adding water into the glass. Each drop dilutes what you get from that drink. The same dilution happens when you add non-essentials to your story.

How can you help them see what you see?

I covered this one a little bit in the section about audience, but there is a special case that deserves its own section.  

Founders are creators. They are the parents of a bouncing baby business that is going to grow up and conquer the world.  They are proud of what they are building and see their business from a place of unadulterated love and excitement.  

Some founders (clearly not you), fail to imagine that outsiders don’t implicitly know the same things they know.  Sometimes the audience doesn’t “get it”. Some of those times, it’s because you didn’t tell them something they needed to know so they would “get it”.  Something that sits in your head and seems so obvious to you that you think you don’t need to include it in the story. When I sit down with founders, I often hear great insights and information that somehow didn’t get into the pitch. When I ask why, it’s usually because the founder just assumed that “everyone knows that”.  If your story hinges on key information, don’t assume that everyone knows that info.

Remember when you couldn’t see the typos in your term paper and needed someone else to put “fresh eyes” on it and help you see what you couldn’t?  Founders should speak with people unrelated to their business and discover what people need to see to share their excitement..

And this doesn’t just go for pitches.  This applies to all stories. When you tell someone about something that “John at the office” did today, ask yourself if you’ve given them enough context about John to understand and appreciate the story. Is John your boss, friend, company jerk, new hire, etc.? People don’t always know what you know.  Make sure that the things they need to know are in the story. Context and insight are key.

The End

The fact is that good storytelling takes more than a single blog post to teach. But whether you work with a storytelling coach or not,  I will say with some certainty that if you are mindful about the things mentioned above and make a few tweaks to all of your stories, you’ll start to see how storytelling should be a tool in every founder’s arsenal.

Before I go, I have to pay homage to one of the great founder/storytellers, Steve Jobs.  He understood the power of stories to affect hearts and minds. Here is a video of his iPod launch in 2001.  Clearly the man knew what he was trying to achieve.  There’s no reason you can’t do the same.