Working with Founders

We recently sat down with a wonderful panel of Assistants to discuss the differences between Assistants working with Founders rather than CEOs or other C-suite Executives.

We talked about working under pressure, supporting a visionary, collaborating and encouraging a founder to delegate. We discussed the challenges of working at the beginning of a company’s formation. The Assistants also shared their tips on staying in the loop and communicating effectively.

The panellists are:

  • Renee Viens, Partner Executive Assistant at Underscore VC
  • Heather Taylor, Senior Executive Assistant at Insurity
  • Lucy Kay, EA Co-Founder and CEO at Redeemeum

Nicky
It’s such a pleasure to have the three of you with me on this discussion about what it’s like to work with founders. There’s a slight difference between working at the height of the c-suite with CEOs and Chairpeople of organisations compared to founders.

There’s a nuanced difference, which we’ll get stuck into today. So to start with Renee, I’d like to understand what you think the differences are between Assistants who work with founders compared to CEOs and other c-suite Executives?

Renee
Because these companies are started by someone very invested in what happens, and you know, it’s like a reputation management type thing. They want everything to be a certain way. They have a vision. And many of these people, I mean, this is their baby.

So they want to approach it as they’re trying to be as careful as possible with how they present things. So when you think about supporting these people, first of all, you have to be very nimble and agile, and there’s going to be a lot of change. And so your communication with somebody needs to be at the highest levels. That’s so critical. I think people need to know that. You’re connected to this person when you strap in for this rocket ride because many of them are startups. So you need to maintain a very high level of communication.

Lucy
You have to wear multiple hats, especially when the founder probably does. They might also be the CEO, for example. So their role is pretty diverse. And therefore, what they need from you is to be agile, as Renee said. And I think you might be helping to operationalise many things to set up processes that aren’t there. And so you’ve got to get on-boarded with their vision and strategy precisely because it’s their baby. And you need to mirror their mindset.

Heather
So having 20 years of experience as an Executive Assistant, I feel, brings a lot of value to them. Because we can make decisions quickly. We know what meetings need to happen, and we can prioritise because they have a lot of demands on their time. So managing their time and being helpful adds a lot of value. Not waiting for permission is something that I’ve learned to do. I put those meetings in and move things around very quickly.

Nicky
Not asking for permission, I think that can be so scary for Assistants, but it’s precious. It’s when you’ve got that confidence to make those decisions. It comes with a lot of experience. Still, I wondered if there was a moment or a realisation that has helped you feel that you can be proactive and make those decisions on behalf of the organisation and your Executive?

Heather
I have to say; if I screw up, it’s okay. I’d rather make a mistake and ask for forgiveness later. So, taking that leap of faith and just saying to hell with it, I’m doing it and making the meeting happen. I’ve learned that over time everything goes smoothly, everything is working well in the calendar, and then they start to rely on me more.

They will leave the calendaring to me, and I’m in charge of that. They adapt quickly. Because once they see that, they can trust you and that things happen. The more they rely on the Executive Assistant. It’s more beneficial to the company and minimises risks to the company. So back to the point of not asking for permission. Tell me if something needs to be course-corrected, and we’ll do it immediately. But that takes time. I’m getting, I guess, bolder in my years of experience.

Nicky
It’s an important point to make. Because I think for Assistants, you know, at specific points in their career, it could be that they are worried about making those decisions. But I think it shows that with experience, you realise that you know what you’re doing. And actually, as you said, not asking for permission is precisely what you should be doing.

Heather
I’ve learned from the greatest; I will quote Melba Duncan here because she taught me well. Executives don’t know, so they rely on us to make things happen. I’m learning that more in my role. And I think it’s a more extensive discussion. But as women, we tend to wait for permission to do things. That is something I am working on for sure. I would encourage young Assistants coming up in this field to adopt that characteristic and see around corners.

Nicky
One of the areas in that Assistants can add value when working with founders is understanding the amount of stress that founders are under and the added pressure that comes when it’s somebody’s business. So I wonder just how you’ve gone about helping your executives deal with the stress that they’re under. And any advice you can give for Assistants who work with founders and other CEOs with real stressful and pressurised roles?

Lucy
They’re inevitably going to have a lot on their plate. So be efficient with your communication. You don’t want to add to their plate by overloading them with things. So managing their time and how you interact with them is essential, and then assessing and deciding how to utilise their time best. So let’s say they’re travelling. Who else can they meet from the network whilst they’re there? Let’s take those decisions off their plate.

You have to get to know them first to make those decisions. But you can take those risks over time, so they do not have to worry about things. You’ve already done it. Is their inbox just a mess? Can you spend some time organising it, putting a system in place and then agreeing on a system with them? You know, have they got too many meetings that are kind of redundant or overlapping? Or do we need to analyse why they’re spending this time? So all those sorts of little ways to relieve stress, I think, help. It comes with having a real awareness of the organisation as well.

Nicky
You cannot get away with working with the founder and not knowing the business and understanding the strategy of the organisation and the objectives.

Renee
We have a good barometer for what’s happening. Access to your Executive’s inbox is essential because you can see in real-time what’s happening at the moment, and you’ll have a sense of when it is a good time to bring up this topic. We use a structured calendar system and block certain things into specific dates and times, so we have cushions between meetings because there is a lot of pivoting. One of the critical things is to build in time for your Executive to be able to shift mental gears. People don’t always think about that. They’re like, oh, you go to this meeting, you go to this meeting.

Well, a lot of Executives, the way that they think, and I’ve seen it up close and personal, is they think ten steps down the road and ten steps back. And they do that in scenarios, right. So they’re looking at all these outcomes and thinking through the different scenarios. And they do that maybe five or six different ways, and they look at the result, then they come back, and then they pick which one they want to do. So there’s a lot of pivoting going on all the time. So you need to leave blank space and do not disturb space for your Executive to be able to think about those things and kind of turn the gears a little bit so that they can decide, okay, how do I want to tackle this.

Regarding the calendar and structuring, it’s imperative to leave them thinking time. And then, as I said, sanity cushions in between. It’s like, okay, I just finished this massive meeting; I need to decompress now and take everything in that just happened. Another thing to mention is don’t text your Executive during meetings because that will disrupt the flow of what they’re working on. So really think about your communications, how you are interacting, and when you are interacting, and stepping into that person’s shoes, and saying, what are they feeling right now? And then that’s how I think we engage our empathy, to let the Executive know, I’m thinking about you this way so that I can understand where your mind is.

Nicky
Yeah, I mean, there’s a tremendous amount of stress taken away when your Executive knows that you’re an Assistant who’s got their back, you know, just that in itself. And you’re there empathising and understanding what their day looks like. That’s a massive amount of stress taken away from an Executive surrounded by people who are taking from them, you know, rather than someone giving to them.

Heather
It also comes down to the Executive’s style. Every Executive works differently. I’ve always tried to encourage not having the back-to-back meetings and meetings glued to each other because things run over and time slips away. But it’s also being empathetic and understanding. All right, now would be an excellent time to have a Diet Coke.

It sounds silly, but I take that to heart because they’re busy, they’re in the back-to-back meetings, or it could be just a simple coffee to bring them. And I’m quite happy to do that. Because it’s a small startup company, I know all the demands and pressures on their shoulders. So just doing that can make their morning. Be intuitive to those things.

Nicky
It doesn’t have to be complicated. Sometimes it is the simplest things make all the difference. Grabbing someone a coke or a coffee is helpful. It’s not a complicated thing.

Lucy
Make sure they leave by a particular time to get home to their families. We need to gatekeep. I think that’s what we’ve all been alluding to and pushing back a little bit. We’ve all said it in different ways. But protecting their family time is also really good. If they have a PT session, ensure they always get to it or have time with a coach. Don’tsacrifice those things for an investable. Make sure that you protect both sides.

Heather
I put vacation time in their calendar, which had not been done before. It goes back to my point about not asking for permission and being bold, confident and decisive. Of course, it could get moved. They might not take it, but I’m there to protect their well-being, so they don’t burn out.

Nicky
There are a lot of founders that will want to control everything because they started the organisation. So they were finance, HR, and everything before they began to employ people. I know, owning a business myself, how hard it can be to give up control of aspects of the company. So I wondered if you have advice you can give to Assistants who work with Executives that may be struggling to delegate.

Renee
So I think we need to look for opportunities. There are always opportunities, especially when we have access to the inbox. When you sit down with your Executive and have your weekly one-on-one or your catch or cadences with your Executives, sit down and say, okay, what are your priorities this week? Maybe there are like five things that have to get done. And then what are the nice to have items, and then the lower priority things. If you can go through that list together, you can pick out one or two things and say, listen, these are less of a priority, but I know that they still have to get done. Would you let me take those, and, you know, even if they’re a medium or a low, the Executive can tell you verbally and say, I have to take care of this. And I have to do that. But yeah, I could let that go. If that doesn’t work, you could say, where do you think I could be most helpful?

Or just like Heather said, be confident and say, you know, I can take that off your plate? And just let me handle it. And then if I have a question, I’ll come back to you. And I think when we start doing this, they begin to see that they can trust this person. This person is competent and can handle these things. They will let the leash out a little farther every time you meet. And you gain their trust. We work with people who don’t have time to always run to the bank to get money, or, you know, maybe they need to change something in their online login for something. And these are things that consume too much time for them. And it’s not worth the dollars they’re being paid to run the company. Whereas, you know, we’re able to take care of things that are a little more, you know, medium and low. Not that we don’t do other things too, but make their day a little more straightforward. So I think going through those together as an exercise and curating your weekly list.

Heather
I like to bring solutions to problems, and when I go to my Executive, it’s like, okay, this is what happened. But here’s how I fixed it. And here’s the solution. The last thing I want to do is overload them because they have so much on their plate. Sometimes we need their input, feedback, direction, and guidelines. So really being succinct in our communication. When I do my one-on-one, I’ll list all my items. So I don’t forget anything. And I take notes there. So I’m able to go back and capture any takeaways. And again, every Executive works differently. I work for two that are entirely different. So it’s like being a chameleon and adaptable to each person’s style.

Lucy
I use Asana, and you can sync that to your inbox and any actions or tasks you think the CEO or the founder doesn’t need to do, you can pick up. If you’ve got a private board, you can also suggest who could do the task, and I always do that. I’m not deciding for him, but I’m saying could X person do this? Then I know the next time I see this similar task, I’ve already forwarded it to that person without asking. We don’t have an office, so Trello or Asana are critical tools to get things delegated efficiently and do things ourselves. But it also helps with delegation; having that oversight is excellent.

Nicky
A founder’s enormous task is to keep moving forward with the organisation’s vision. As Heather said, they are the visionary behind the organisation. So I wonder how you stay in the loop with what’s going on, what the strategies and objectives are, and how you help your Executive communicate that across the business.

Lucy
We do have a weekly company-wide call. I get the founders to be on that every week to say something, as long as there’s something relevant. We also have weekly leadership meetings. I organise those to see what gets disseminated, how it gets disseminated, and how information flows through the company. I also run the OKRs. So ensuring senior leadership, managers, and everybody has objectives and key results.

Managing that process, you see where we were at in our roadmap. I sometimes listen to calls in product teams just to know what’s happening because there’s so much going on. And if I have time, which is rare, I try to dip into product calls and listen. I give feedback a lot to my CEO and say, we all know this update, but the rest of the team doesn’t know it yet. When is a good time to deliver that message?

Renee
That’s why it’s imperative when Assistants are looking for a role to find something that interests them, that they’re excited about and want to be involved in because it gives you more opportunities to flesh out and develop your skills and talents. You can find projects or tasks that excite you.

Taking an interest in one part of the business that is interesting to you, whether it’s working with somebody that has a marketing task, or, you know, communications or whatever that might be, and then really taking that piece and running with it. When communicating or talking to other people in the company, tie that back to an actual goal. It helps to pay attention and absorb as much information as you can. So that when you do communicate on behalf of your Executive or the company, you’re connecting it to and laddering up from that goal.

Nicky
Renee, I know you’ve just gone through the interview process. I wonder if there are any things Assistants should be looking out for when they apply for a role with a founder that they might not have thought of when working in the C suite or with a different Executive.

Renee
It’s important to know yourself. Knowing what you are looking for, make your pros and cons list, and look at the things you are interested in. Find out what things you have in common because you do need a common basis to work with someone that you know is going to match what your goals are for your career and your skill set. You have to ask hard questions.

There have been a couple of roles that I’ve looked at, taken, or whatever, and I avoided some hard questions. And it doesn’t always turn out the way you think. Because you’re like, oh, I should have asked that. Is this person a morning person? Are they, you know, are they super engaged in their community? Or their network of people? Like, what are their interests, because you want to find common ground when you meet with people. And if you have that as a basis, it will be wonderful. So think about the things you don’t want, which will help you focus on what you want. So definitely make that list and separate things; it will help you clarify when you start interviewing.

Heather
Ask the question, how do you like to work with your Assistant? What is important to you? How do you see that playing out? And is it shared communication? And does there have to be alignment? Drill down even deeper. How does one like to work? Do you want to meet with your EA at the top of the weekend? At the end? How does the communication work with everything being remote? Do you like to text? Because if you don’t ask those hard questions at the start, you won’t know if you are in the proper role.

Nicky
Many startups now have founders who may have never worked with an assistant before. They’re just getting the organisation off the ground. I wonder how Assistants support founders who are new to all of this?

Heather
It’s not easy. Let me just say that, let’s not kid ourselves. That is not easy. So accountability is essential. Demonstrate delivery and execution. Those three things will show your value to the organisation and their business goals. So, and again, trust is built over time. I go with the adage that Rome wasn’t built in a day. We take it step by step, day by day. Transparent communication is essential and critical. You have to like each other. When you like each other, there is trust, warmth, and kindness. Those are non-negotiables. For me, more so than salary. Salary is just the icing on the cake. Don’t be hungry for the money. Be hungry for that partnership, that communication, and trust. It’s not going to be perfect, nothing is perfect, but you have to like each other to work well together.

Nicky
And sometimes it’s about taking the risk, isn’t it when you work for a startup, it’s going on that journey and seeing where it takes you and sometimes that’s not for everybody. But amazing things can happen when you’re right at the start of the incredible journey with an organisation.

Heather
Because they’re so deeply committed, they’re visionaries. They are deeply committed to the business and want to see it succeed. And so, I think part of my pride is in being part of that accomplishment, part of that drive to make things happen and for them to succeed.