Every startup employee at some point has an idea that they believe will create a lot of value for the company. How do you get the greenlight from the CEO so you can turn the idea into reality? Startup CEOs are ambitious, under immense pressure, and extremely time poor. That means that if you want to propose a new initiative you’d better do your homework and prepare as well as possible. Here are seven steps to make sure your project gets the resourcing and backing it needs to be successful. This should be an obvious step but for far too many people it isn’t. You have to be as specific as possible in showing the impact you expect this initiative to have. That means having a key metric. Make it direct and measurable — don’t leave it to the imagination or make it vague. “This should increase signups” is a bad example. Instead this should be: “Our target is to increase the conversion from visitor to signups by 10%” If it’s not clear what you’re trying to do then the answer will automatically be “no”. You have the key metrics you’re measured on and care about (if you don’t then that’s a much bigger problem) but why should the CEO earmark your initiative for resources? The answer is that your numbers drive the metrics both the CEO and the rest of the company care about (if that’s not the answer then you should abandon your idea immediately). There are always top-level numbers that matter to everyone in the company like revenue, profitability and cost. Your numbers should already be tied to those higher level figures. Even still you should connect the dots for your CEO. This makes the full implications of the resourcing decision obvious to the CEO. That might sound trivial but it isn’t. You add value when you communicate succinctly with decision makers so they need to do the minimum amount of mental lifting. This is important when you consider how much decision fatigue your CEO probably has. Good startups use lean startup methodology to rapidly iterate from their initial idea to product-market fit. This approach works for initiatives at all levels in the company and your proposal is no exception. Let’s say you’re a real estate rental startup and you want to create a “Should I Rent Or Buy In My City?” calculator because you think renters will find it useful and that it’ll drive pageviews. You want the CEO to let you spend money on an engineer to build this calculator. A good test would be to pick just one city and do a “Rent Or Buy In City X” blog post and see how many pageviews it gets. Make sure you pick the right metric and definition of success before you run the test. The metric for success should be as close to the number you’re trying to move with the overall initiative. In this case, that’s pageviews. What’s a better pitch for your CEO: “I just know this will work in my gut” or “I believe in it so I tested and when we did the blog post we had 1,000 people spend 7 minutes on the page.” The answer is obvious. What happens if the test ‘fails’ and you don’t see the numbers you were hoping for? That’s a great outcome! You’ve just saved the company previous time, energy and resources by cutting an initiative that had a low chance of success. If you’ve followed the steps until now and your idea is still standing then you’ve made the case that you need resources. The next question is how high up on the roadmap should your initiative sit? There are several factors that go into prioritization: expected upside, how confident you are in getting the results described, the amount of resources it’ll take, resource availability, time to execute, and the other items on the roadmap.1. Know the key metric you’re trying to change
2. Know what metrics your CEO cares about
4. De-risk by testing
5. How to get priority
If you think your CEO has accurately gauged these factors for each item on the roadmap then you should trust wherever they put it. You should only advocate for moving your initiative up the list if you think your CEO isn’t weighing the factors correctly.
Just remember that your CEO has information you don’t have and there may be things they can’t tell you. For example, a key engineer may be leaving soon but it hasn’t been announced. Passion is important but ultimately you have to trust your CEO and their judgment.
6. Get input from a smart colleague
If you notice someone in your company is really good at getting CEO approval or seems to be able to read them particularly well then pull them aside and ask for their advice. If you can make them an ally in your request then they can probably look over your proposal and give feedback on how to make it stronger.
This is especially helpful if your CEO is intimidating, difficult to convince or hard to read. You may only have one shot to get them onboard and you better make it count.
7. Make it easy to say “yes”
Your CEO’s time is rare and valuable and you should treat it as such. Make sure that when you make a request you express it succinctly, give them all the key facts, format your request so it’s easy to read (bullet points are your friend), and pick the right time to make the request.
Everyone has their preferred system for decision making. Your CEO may prefer to have office hours once a week for considering these requests or they may funnel them all through their inbox where they’ll handle ad hoc.
If your CEO has an executive assistant then check with them to see if the CEO is going to be in the right mood when you approach them with your idea. This one step alone can make a huge difference.
Don’t forget that you and the CEO have the same goal and want the same things. Keep that in the front of your mind and trust the process above then you’ll add more value and have fewer failed initiatives in the long run.
If you've got a good idea - something that can help your company, or your career, or maybe both at the same time - you've got to convince your boss to get on board. You know you need to pitch your idea in a way that's simple, clear and compelling - but what's the best way to do that? Let's face it: one idea, together with a great pitch, can redefine your career. How do you craft a pitch that doesn't sound like a sales job, or a data dump - even if you work in sales, or data? These seven proven pitch strategies will help you to clarify your message and help your boss to give your ideas the green light.
The conversation that can re-define your career: pitching your ideas to your boss.
Getty- First, Answer These Two Questions: There are two questions on your boss's mind right now. She may not tell you what they are (but I will). When presented with any new idea, here's what shows up right away: How much does it cost? And: how much does it make? An effective pitch has to be clear on those two questions. Got your numbers? OK, hang on to those answers - you won't open with them, but you'll need them later.
- Then Start with a KISS: that stands for Keep It Simple, Stupid (of course). I'm not suggesting you kiss your boss, no matter how much you think that might open up the conversation (or start one in HR, maybe). I'm saying that the simplest message is the strongest. Don't over-plan! If you walk in and say, "I think we need a new 50,000 square foot warehouse in Hoboken!" your attention to detail will only be an invitation to an argument. Why 50,000 feet - why not 35, or 60? That's what your boss is wondering. Then you get peppered with questions about which location in New Jersey is really best. It's better to KISS, with respect: "I want to talk with you about some ideas for the new warehouse location, and I think New Jersey might be perfect for us. Can I share what I've been researching?" Mwah! that simple question opens up the dialogue. Walking in with all the answers is a quick path to disagreement - especially if you are convinced you are the subject matter expert (SME). Don't invite your boss to a wrestling match regarding the merits of Hoboken - there's a stronger approach you can take.
- Ask, Don't Tell: Asking for advice and guidance helps get your boss involved and enrolled in your ideas. Jack Stack, in his international best-seller A Stake in the Outcome, says that "people will support what they help to create." Owning your expertise, and your ideas, means you can extend that ownership to your boss. Let her know that her ideas matter, and that she's actively involved in the decision. Even if you know the exact street in that industrial area in Hoboken, it's best to ask for input. That's not manipulative - that's good business! Don't you want her input - or just a rubber-stamp of approval? Because, no matter how much research you've done, remember that none of us is as smart as all of us. Approval is necessary, but insight is priceless. Don't leave the meeting without it. You're talking to your boss because you want her contribution - so make sure you get it.
- Context Conquers Content: The great comedian, George Carlin, used to step on stage and say, "Here are the sports scores: 7, 21, 9, 16. And a partial score from the Notre Dame game: 11." Without a frame of reference, the numbers don't mean much. Are you dumping data without the right frame of reference? It's easy to get lost in the content of your pitch. But actually, it's context that really counts. Without it, your story doesn't make sense.
- The Presentation That Matters Most: in every presentation I give, and I will give about 65 keynotes this year, there are always two speeches: the one that I give. And the one that the audience hears. Which one do you think matters most? Make sure that you know what your boss is hearing in your presentation, not just what details are on slide #47. Because the best presentation is always a conversation. The sophisticated presenter knows that a powerful pitch is really a dialogue - make sure you find out what message is being received, so you can course-correct mid stream if needed.
- Invitation Over Instruction: are you trying to teach your boss what you know - or invite her to a shared discussion to identify the best path forward? In my work with clients on shows like Shark Tank and Dragon's Den, we talk about the dangers of instructing the Sharks and trying to prove you're the smartest person in the room. Ever see someone tell Mr. Wonderful anything about wine? Yikes - Kevin O'Leary comes back with guns-a-blazin', making sure his sommelier-crushing expertise takes center stage. Invite the expertise into the conversation, don't challenge it. If you're working hard to establish your credibility, it's time to bring some emotional intelligence into the conversation. I'd like to invite you to look in the direction of service, not instruction. What would you say if your expertise were a given, and you didn't have anything to prove? What changes in the conversation now? Perhaps looking in this direction will point you back towards service and outcomes - which is really what your boss is looking for.
- Speak in Leadership Language: I was working with a client in Hungary. He spoke five languages, including perfect English, and I asked him a dumb question. "Eric, why are we speaking English today?" His answer was an easy one: "Because that's the only language you understand." Leadership language is the language of your listener. Take time to really consider what matters most to your boss. What are the phrases that will inspire her, strengthen her career, and make her the hero of your story? I'm not suggesting you work on crafting an elaborate fiction around the merits of Hoboken. Focus first on what the C-Suite cares about. By speaking your boss's language, your initiative unfolds in a way that's easy, accessible and clear.
Bringing your ideas to your boss can be a little scary, but your pitch doesn't have to be. Because it's not really a "pitch": you're not going to speechify anyone into submission. You're inviting your boss to an event that you host every day: a simple conversation. A conversation that speaks her language, in a way that starts simple so you can dive into the details, one step at a time. By asking for feedback along the way, you gain the guidance you need for your journey. Take time to consider the conversation that will serve your ideas, and your company, best. If you've thought through your ideas, you know how much they cost, and how much they will make. Now it's time to make good on your pitch - and gain the insight you need from your boss. Time to level up, and gain the support your ideas deserve!