It’s All in the Ask. How to Get the Professional Support You Need Right Now

“The truth is, if you can’t pitch, you will not get the support you need,” said Debi Kleiman, seasoned marketer, educator and entrepreneur, who now leads the Blank Center for Entrepreneurship at Babson College. Most people don’t know how to ask for what they want. Yet, connection to that job, mentor, advisor or investor, comes down to how you ask. And many of us hate asking for support! Even when there’s a mutual value exchange.

As millions reinvent in this pandemic, support for your work or business, will mean building relationships in new ways. Debi, my former colleague and friend, distills the fine art of professional persuasion in her new book, First Pitch! Winning Money, Mentors and More for your Start-Up. When she began teaching, she couldn’t find resources on this topic for her students. She said, “It made me sad that to think there were people who were not being heard in the world because they were either afraid or didn’t know how to tell their story.” Debi’s sage advice can help you move your vision forward, even in tiny mom-bytes of time.

Mind The Career Gaps

Results from decades of trying to close the wage and leadership gaps have been underwhelming. Only 1/3 of women try to negotiate better salaries and when we ask for raises, we are less likely to receive them and more likely to face negative fallout. These dismal statistics have inspired more women to start businesses and side projects. Now, the COVID19 economy and record unemployment, only heightens the need for professional allies.

Debi explained, “If you’re incredibly passionate about your idea, just by talking about it in the right way, you will get other people passionate about it too. And I’m not just talking about the investor pitch. You are probably going to be pitching for your first customers, employees, mentors and advisors.” Exactly this. Moms, still knee-deep in childcare and household, tend to place efficiency over career coalition building. But you can learn effective outreach to make those dream connections.

How to Ask for What You Want at Social Distance

Incredible things rarely happen in isolation. Relationships can turbocharge the path to meaningful opportunities. And whatever your goals, expert guidance will move you closer. The idea of pitching might make you wince but it’s rarely about selling and we all need to communicate our ideas. Debi explains, “Pitching is one of those essential skills in entrepreneur land that you have to nail.” It may feel daunting in the current climate but it’s required in every field. Debi wisely states, “it’s really about business communication and building relationships. I say it about 10 times in the book, pitching is personal and the biggest change is that you have to do it all online now. It’s about the relationship you’re creating with your audience, whether it’s an audience of 500 or one.” The fundamentals are the same and you can tweak the mechanics in the era of lockdown.

Like Online Dating but Easier

There’s nothing quite as intoxicating as finding someone who believes in you. When it happens professionally it can make all the difference to career success. Whether seeking a mentor, boss or funder, Debi explains, “We are there to build a relationship with someone. They have to fall in love with you and want to help you so much, that they just can’t help themselves. You just have to be cognizant that’s what you’re there to do.” It’s going in with the intention to spark trust and mutual interest. Debi said, “It’s harder to build relationships online but not impossible. People do it all the time, you know, online dating!” I laughed. She added, “There are tactical things that you have to remember to do differently. I think listening to someone pitch for 20 minutes online is really hard, so you have to break it up more. For example, use more slides online so visually the environment is changing more often. You have to have a good headset and technology. I also recommend standing when you pitch online. It helps your breathing, your energy and you come across as much more professional.” Awesome. The little social touches that are natural in person can work on video. Debi said, “It means spending more time. Talk about where you’re from and what’s in the room at home, find ways to connect with the people you’re pitching to.”

Listen Hard for What’s Changed Post-COVID

If you have a target audience or an existing one, open up a dialog. Debi said, “Talking to your customers right now is probably the most important thing you can do. Really understand what they need from you, not what you want to give them but what they need and will need from you in the next 18 months.” I smiled, because we worked together at a market research agency. Debi is frequently sought to join boards and mentor entrepreneurs. She said, “When someone comes to present to me, if they’re not showing me some really interesting insights they’ve learned from talking to their customers, I’m probably not going to be super bullish, because they haven’t done the work. I’m looking for founders who acknowledge the world has changed and are reflecting the new reality in their business plan.” Yes! A great reminder for everyone’s professional outreach.

Yes, You Can Overcome The Barriers

Seeking investment, in the midst of the biggest global recession since 2009, is scary. Funding for women led businesses was already around 2% and half of that for women of color. Debi said, “There’s a whole chapter in the book about bias in the pitch process for female and underrepresented entrepreneurs. Today, the process is very biased and that’s because traditionally it has been the iconic white male entrepreneur in a hoodie that people expect to see. There’s this sociological phenomenon called homophily where people want to like, trust or invest in people like themselves. The industry is really broken on that front. We know from research that if there’s a woman venture capital partner evaluating a woman-led company, they are 3 times more likely to make that investment!” As we look to a brighter future, there are still ways to improve our chances of success.

The ‘I’m Confident’ Superpower

Debi said, “When Columbia Business School researchers analyzed pitches for venture capital they observed females were asked ‘prevention questions,’ you know, ‘how do you stave off doom?’ whereas male presenters were asked ‘promotion questions,’ about growth, vision and big picture thinking. We know from that study that the questions you get asked really matter. People who were asked mainly promotion questions raised 7 times more money than people asked mainly prevention questions. So, you have to be able to recognize that. Basically, you’re going to get asked a question you don’t want to answer and then turn it into a question you do want to answer.” Love that. She added, “It takes practice. So, if you notice a prevention question coming your way like ‘how are you going to retain customers?’ you immediately start your answer with, ‘I’m confident that.’ As soon as we say, ‘I’m confident that’ we actually feel more confident. Then, turn it into a question about growth, for example ‘I feel really confident that we’re going to retain customers by doing this but also, we’re going to tap into this new segment that’s going to be an incredible growth area for us’ to launch into that piece of your plan.” Brilliant!

Take Action Even Tiny Ones

Many of the Moms I meet have extraordinary ideas they shelve for ‘someday’ when there’s ‘more time.’ The days dissolve with interruptions. And new initiatives take time and energy. Debi said, “Sometimes moms worry that being a mom is a negative in the world of entrepreneurship but moms get more done before 8:00 AM than everybody else and after everyone goes to bed, we’re still powering through stuff! All the mom skills are necessary to be good entrepreneurs.” So true. She said, At Babson, we teach this idea of ‘taken action.’ Take the action, learn from it and then take another action. So, it’s a cycle of ‘act, learn, build.’ A lot of people think the cycle is ‘plan, do, build’ but it’s not anymore. It’s this very iterative process. Just do one thing that’s going to tell you something about your idea. You can break it down into tiny little chunks of getting stuff done and by the end of a month, you’re going to start to see something real towards your goal. It’s not like you have to take this big bold move all at once.” Yes!

It’s tempting to freeze with the amount of financial pressure and uncertainty that surrounds this pandemic. Especially as we try to work and plan, surrounded by our loving families, all-day-long. Unlock the opportunities you seek with the ask. As Debi wisely states, pitching is much bigger than funding or even entrepreneurship. It’s a core skill that when exercised, will ultimately improve the climate and receptivity for women’s professional ideas and contributions.


Has your life changed in the past couple of months? Please take this quick survey to share your experiences of  the pandemic.

Many thanks to the amazing Debi Kleiman! Check out her new book, First Pitch, How to Win Mentors, Money and More for your Start-up, and follow her great adventure on Twitter and her website.

Debi Kleiman is an award-winning marketer, teacher, startup advisor, mentor, and angel investor, with over fifteen years of experience working with and coaching startups of all kinds. She is the Executive Director of the Arthur M. Blank Center for Entrepreneurship at Babson College, the #1 school in the nation for entrepreneurship. A marketer at heart, she previously spent a decade leading initiatives in brand development and innovation at Coca-Cola, Welch’s, and Procter & Gamble.

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