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I don't know what I don't know...

"I don't know what I don't know" is a phrase I've heard at least once from each of my one-on-one coaching clients. I deeply understand this sentiment, as I've experienced it myself at various points in my career and while starting my own business.

Below, I've outlined four of the most common scenarios in which this phrase has come up in my conversations. I've talked to founders, individuals leaving the corporate world to start their own business, and sales leaders. While the subjects may be grounded in sales, the framework and thought processes behind them can be applied to any area of your life.

I don't know what I don't know...

1️⃣ Re: Setting sales goals and hitting my revenue numbers: If you're not working for a company that provides this structure for you (e.g., you're a founder), figuring this out can feel daunting. Here is a simple way to start:

1. Use Google sheets and work backwards from your end-of-year total revenue goal. Create rows and columns and include every revenue stream that you have for your business. Play around with various scenarios to see what combination of offerings you will need to book to hit your end-of-year goal. Eventually, you will also learn and incorporate the length of your sales cycle, which is the average amount of time a piece of business takes to book.

2. Talk to as many people as possible who have started a business or set their own sales goals. Ask them, "What do you wish you would have known when you started?"

2️⃣ Re: Setting up your infrastructure and organizational tools: Much of this will depend on YOUR style and what works for you. I personally like Asana for organizing my tasks/projects and Hubspot as my customer relationship management (CRM) tool. In the corporate world, I used Salesforce. If you're involved in a customer-facing role, you'll want to track key information and communication with that customer. Even if you have a great memory, once you're talking to various contacts, you will forget. Plus, you can trace and set dates to follow up. Both of these systems allow for other members of your team to join, which is crucial as you scale your business. Hot tip: there are many resources online ranking the various tools, as well as YouTube videos highlighting ways you can set up the tools to best work for you.

3️⃣ Re: Determining the cadence of your sales outreach: Many companies focus on creating sequences for sales outreach, which is essentially scheduling the number of days between calls and emails and even drafting the communication you use for each. In my opinion, I prefer personalized communication that isn't formulaic. One of my co-facilitators at a sales training last week summed this up eloquently: in talking to customers, you are balancing that line between building a relationship and moving your agenda forward. When in doubt, think about the times you've been sold to; you can tell when someone is following a script versus taking the time to find a commonality with you and personalize their approach. Who would you want to buy from? Think about what is important to the customer and reach out with their needs in mind.

4️⃣ Re: Handling difficult conversations and customer objections: This aspect of selling always feels intimidating, but a reframe is that you have an engaged customer and can learn a lot from these situations. The first step is to prepare. Write down your most common objections or anticipated objections (e.g., price) and then start to draft talking points. The second step is to recognize that you can only prepare to a point; unexpected surprises will always come up. When that happens, take a deep breath and seek to better understand. Don't make assumptions, even if you've faced that particular objection many times. Ask questions to get to the underlying concern or problem.

When in doubt, the fastest way to accelerate your learning is to learn from others. Don't be shy in reaching out to others that have forged a similar path, and take advantage of all the resources and communities you can find online. You've got this!

What else comes to mind in your work or life when you think about "I don't know what I don't know"? If you input your response(s) here, I will include my thoughts in future content.

Would you like to continue the conversation? Please do schedule time to chat; I would be happy to dive in with you.

I share different content (resources, helpful tips) on different platforms, so please feel free to connect with me via the below. And keep an eye out for content that will help you in your day-to-day life.



One of the first photos taken for my website as I was starting a business and navigating how to figure out "what I don't know".

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