How to be real with investors: advice from a CEO with a newborn

In the fast-paced world of startups, it can be hard to know what to do when life events force you to slow things down or take some time out.

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For many business leaders, there’s one thing that causes particular anxiety when the personal spills into the professional: the opinion of investors.

From fears of losing their confidence to concerns about your next funding round, letting investors know that your personal circumstances have changed in a way that might impact work can be daunting.

But CEOs are normal people grappling with real lives, just like everyone else. From pregnancies to bereavements, when life happens we must decide whether and how to share personal news with investors.

The pressure of personal updates

There’s often an unspoken pressure for CEOs to demonstrate a kind of all-consuming devotion to the business, especially in startups. Fears over how investors will respond to personal updates can dampen even the most joyful news – or make a stressful situation a whole lot worse.

Many will tell you that this pressure is often felt more acutely by women who still struggle to be taken as seriously as their male counterparts. I was taken aback when it was suggested to me by a well-meaning VC that I hide my pregnancy via Zoom calls, for example.

Ultimately, I had an extremely positive experience with investors. My existing investors were hugely supportive of my pregnancy; and if any potential future investors weren’t, it was a serious red flag not to work with them.

How to get investor conversations right

But, there is an unavoidable power dynamic at play. It’s so important to get investor conversations right – for your own sake, as well as the sake of your business.

I knew that if I wanted my needs to be understood and accepted, I had to communicate my personal news with care.

So, drawn from recent experience, here are five things CEOs can do to make the nerve-wracking investor conversations about the “real” bits of life go as smoothly as possible.

Start preparing now

The best way to ensure you can be real with your investors at crunch time is to lay the groundwork for this conversation before it’s needed.

If you know you’ll need to take time out of work in the future (for instance, to start a family), make sure you have a strong, supportive executive team in place that will be able to cover for you when the time comes.

No business should be run in such a way that means things grind to a halt if the CEO is away.

Invest in those around you and build a strong C-suite and leadership team. Take time to consider which colleagues investors will have faith in, as well as any training or handover they’ll need to build faith in their own abilities, too.

This proved invaluable for me during my maternity leave, and went a long way to reassuring investors that the ship would remain steady in my absence.

Be strategic with your timing

Don’t feel pressured into updating your investors the second your circumstances change. The freedom you have here will largely depend on the nature of the news, but, if you can, take your time.

Choose your moment wisely – within reason. Not only will this help to ensure that your message to investors is as refined as possible, but it’ll also give you time to begin to process the news yourself.

And, as a practical point, be sure that your news won’t overshadow any important company updates.

If you don’t have the luxury of time (for instance, if you need to take compassionate leave with immediate effect), be direct and honest about your situation. Investors are human, too and ultimately they want you on top form. If time away from work is what will ensure that, they should be happy to oblige.

Do your research

Remember, as CEO, you’re still an employee. You have statutory and company-specific employment rights, just like everyone else working for the business.

So, make sure to get up to speed with any relevant legal information and company policies before speaking with investors. This way, you can be confident of where you stand and know exactly what support (e.g. parental leave) you might be entitled to when delivering your update.

This will not only reassure investors that you’re well-informed and have a clear plan in place, but it should also allay any misplaced guilt you might feel about taking time out. Things like parental leave aren’t favours – they are fundamental workplace rights.

And, keep in mind that when CEOs are seen to make good use of their various entitlements, they encourage employees company-wide to do the same. This is a great added bonus that helps to build a healthier, more compassionate working environment from the top-down.

Anticipate questions

Changes to leadership, however temporary, will generate a lot of questions. Consider what your investors’ main concerns will be (e.g. will you be absent for an important product launch or fund raise?). Then, make sure your answers show you understand the impact your news may have on the company and that you’ve planned for ways to mitigate this.

Test the water

Update your existing investors, whose trust you’ve already gained, first.

Pay attention to their response and use this to inform your approach with prospective investors. Depending on the circumstances, you might not need to say anything to prospective investors at all.

You also might feel that your news should be shared strictly on a need-to-know basis, which is absolutely your prerogative.

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Khyati Sundaram is the CEO of Applied, a behavioural science-backed tool for fair and de-biased hiring. Applied helps companies remove bias from hiring processes by removing gendered words from job adverts, anonymising applications, holding structured interviews and hiring based on skills.

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