What to Say when you Have a 'Big Ask'
- Jen Stover
- May 6
- 10 min read
Updated: Jun 30

Although our life and relationships are pretty much a continuous exchange of small gives and takes, occasionally life throws us a curveball or we have a ‘Big Ask’, or a big request to make of your partner, a work colleague or family member. ‘Big Asks’ are more than just the usual quick, easy, 'favor'. And they can include situations like:
A need for a change in lifestyle
A need to pursue an idea or dream
A need to try something that’s dramatically out of the 'typical' flow of your work life, or the way your team or marriage typically operates.
Or a need to find middle ground between the needs of a love relationship, the needs of the individual and the needs of another family member.
Nic and I recently worked our way through one of these 'Big Asks'. He wanted to combine a much-needed sabbatical out in nature with working his photography business remotely. But I couldn't join him, as I have plans myself this summer in our current home town and am deeply immersed in a new aspect of my non-profit business. Plus, although we don't have kids, we do have a rambunctious, attention-seeking dog at home that we typically 'co-parent'. How were we both going to get our needs met, be responsible pet-owners and stay connected as a couple over the time he was away? I can say that although we 'mucked it up' a few times, had to backpedal and re-do some of our initially awkward attempts, we did pretty well in many conversations. And we were able to create a solution. So this post shares what helped us foster a safer relational field and maintain connection while worked out how to resolve a ‘Big Ask’.
What we’ll cover:
Part 1 - How to Start a ‘Big Ask’ conversation - including the importance of leading with shared values and mutual purpose, and how to relay your ‘Ask’ so it gets the best reception.
Part 2 - How to Ask for Support so you Actually Get it! Including How to co-create solutions that honor mutual purpose and shared values, and… a powerful Bonus Question (that most people forget to ask).
So let’s get started.

How to begin a ‘Big Ask’ Conversation
A) Timing is essential
As with a lot of difficult conversations, timing is an important factor. So lets just put this out there and call it: A PREREQUISITE: Set aside a time to talk that works for everyone involved.
Granted, even that has some language nuances that can make it more effective. For example: simply saying, "we need to talk later" can sometimes result in one of us unnecessarily creating stories in our head about something catastrophic. That's the nature of our negatively-biased and protective brains. A more helpful alternative that works for us is,
"hey, when you have some time later I'd like to run something by you and would like your input."
A little more casual, a little more inviting...and a little less catastrophic wondering. Get it?
B) What to include
1) Unify - include a shared value or goal as well as what you don’t want to happen. This automatically makes it a ‘we’ issue and not a ‘me’ issue. It sets the tone that this ‘ask’ is relational and involves more than just you.
2) Recognize - Recognition of how your ask will affect others shows awareness and collaborative thinking. IOW, you understand why it’s a big ask.
3) Keep it Simple – On its first introduction, state your need as clearly, kindly, simply as possible. This allows for engagement to flush out details and avoids overwhelm which can erode the listeners belief in their ability to support you. Needed details will come out through questions.
4) Give them a peek (inside your head). Sharing your ‘ideal version’ can give the listener some insight into what you’re thinking and minimizes guessing or making false assumptions. Sharing your conflict also show you’re human and makes you relatable. And relatability creates connection.
Let’s run some story examples. Then I'll share what Nic and I worked out at the end of next month's issue. (Each of the numbered inclusions above will noted in the example below).

Story One – Fulfilling a Dream
Sam and Katie are a couple who both work full-time. They don’t have children, so they’ve intentionally cultivated their lifestyle to reflect the financial freedom that comes from being a child-free, double-earning household. They live in a beautiful condo, love to travel and eat out whenever they feel like it. However, Katie turns 50 this year and is feeling the pull to follow a dream’s she’s always had, but has put off for a variety of reasons – to write a book! But to do it, to fully commit her mental space and to creatively accomplish this dream in the shortest time possible, she wants to quit working. But she also knows it would affect the lifestyle they love, by cutting their income in half. She’s torn, but wants to bring it up to Sam. But she also knows he's a very thoughtful and methodically person and sometimes transitions to new ideas at a slower pace than she does. How can she bring this up?
Example: (after setting up a good time to talk)
“Our relationship is important to me. And so are your needs. The last thing I want is for anything to take away from our relationship(1) And I know we have this terrific house and love to travel and eat out whenever we want (2). But…… I’m also really feeling the need to pursue a dream I’ve always had, by writing a book (3). Ideally, in my world that would mean me quitting my job now and committing to this dream full-time (4). But I know this would also affect you, which is why I know it’s a big ask (2)".
NOTE: In personal relationships, it’s easy to confuse the real need, with the strategy to get the need met. So taking a look at the purpose behind the strategy, can take your conversation to a deeper level. In this example, what unmet need is writing a book also serving? Ie: a need for autonomy? A need for self-expression? A need for legacy?

Story Two – An Unexpected Demand at Work
Justin is a team leader for a fast-growing company. His team is excellent and works hard. In fact, they’ve been working especially hard this last quarter and are pretty exhausted. The company just found out they may lose a critical contract. And Jacob is getting pressure from above to meet an already tight deadline, sooner. He’s done his best to represent his team, set boundaries with upper management around what his team can do without burning them out. And although he did negotiate some leeway, his team will still need to do more than they’re already doing to meet this critical deadline. How can he bring this up?
Example: (after setting up a good time to talk)
“Our company goals and this team’s well-being are both important to me(1). The last thing I want is for anyone to burnout or feel like their input doesn’t matter. It does. I also recognize that everyone is pretty exhausted from this last month’s push.(2) But I just found out that we may lose the Peterson contract, unless we can show them the completion forecast data by the end of this month, which is a lot sooner than we were originally told (3). I did my best to gain some leeway but ideally, this would mean all of us working longer hours for a few more weeks (4) But I know you’re already tired and this will affect your home life and personal plans (2 & 4)".
Both story examples set the tone of unity, showed awareness and understanding of how this ‘ask’ that would affect everyone involved, relayed the speakers relatable humanity and described the 'ask' in a concise, simple initial statement.

So here's what comes next...
Ask for support and encourage engagement
Shut up and listen, taking breaks as needed
Clarify as needed, and ask what’s possible
Then collaboratively brainstorm.
Let's Practice:
The Sam and Katie Story: (continuing from above):
“… I know this would also affect you Sam, which is why I know it’s a big ask. How do you feel about this? Is it something you can support me on?”
She then listens to Sam’s response. He understandably has many questions and some concerns. Katie listens, answers questions as they come up. When things start to get heated, they agree to a 10-minute break and come back to the conversation. Sam can’t support here in exactly the way she would have ideally wanted. Katie just up and quitting her job feels too abrupt to him. He’s more of step-by-step, plan-first-then-do type guy. Katie is more a do-it-and-figure-it-out-along-the-way type woman. Both will need to stretch a bit to bridge their differences. So she asks,
"Okay then, how could you support me? Are there other ways you can see us both getting our needs met? The last thing I want is for either of us be stressed out financially or personally. What I really want is for us for this to benefit our relationship and for us both to be happy”.
And then the brainstorming dialogue begins.
TIP: When something is misunderstood, instead of getting defensive, try clarifying through contrast. “The last thing I want is ________ . What I really want is _____________”
Stay aware of your voice tone and volume. The meaning behind our words stands a better shot at landing if the listener can hear and feel it through both what you say and how you say it.

Let’s see that again with Justin's Story at his workplace (continuing from above)
“…. I know you’re all already tired and this will affect your home life and personal plans. What are your thoughts on this? Is this something you feel we can do as team?”
Then he listens to his team members. They understandably have many questions and some concerns. Justin listens, answers when he can. When things get heated, they take a 10-minute break and come back to the conversation. Not everyone on the team can support Justin in exactly the way he would have ideally wanted. A few are okay with it, some have made family plans, others are sleep-deprived. So he asks:
“Well, how can we support getting this contract ready in time? Are there ways I haven’t thought of that support the company getting this contract, and also get those who need it the rest they’ve earned? The last thing I want is for anyone to burn out. You all are too important to me and this company. What I really want is to showcase what we can do as a team, but without running us all ragged”.
And then the brainstorming dialogue begins.
Notice that with both examples:
Mutual purpose and shared goals were referenced again.
Flexible thinking and receptivity was evident by asking for engagement and then listening.
The biggest takeaway from both these story examples is that..
the words we choose and the tone we use is what creates a feeling of safety.
In both cases, although the ‘Ask’ is indeed challenging, everyone feels considered, cared for and respected. This helps connection remain intact and sets the foundation for relational ‘magic’ to begin.

So what’s that Bonus Question you mentioned? (the one most people don’t think to ask)
It’s simply this: “how can I support you in supporting me?”
Offering return support often gets forgotten but is a really powerful connector. Think about it. How will someone supporting you, impact them? This simple question demonstrates:
a recognition that you're in this together,
that the other persons support matters to you,
that it’s not just about you, and
that you understand that one person getting their need or want met, often involves the support of others. And that support may be a 'stretch' in their part.
In the story of Katie and Sam, Sam may be willing to support Katie in writing her book. But he may need a bit longer time to process and a plan for their loss of income. How can she support him to process and plan for this? What can she do to help him support her? Could she perhaps help forecast their financials? Maybe she could write up a timeline they could work with. Are there ways she could save money now in advance, to cushion the impact of the decreased household income later? See what I’m getting at? Ask your partner what he/she needs. Don't guess.
In the case of Justin and his team, they may be willing to work in shifts to get the task done, but they’re still exhausted. How can Justin support his team in supporting this task? Can he supply breakfast in the office every morning? Do any of them, or their spouses need part-time help at home over the next few weeks? What tasks does Justin usually supervise, that he can do himself to give someone a few hours off? Again, asking what's needed instead of guessing will make your actions more meaningful.
My point is that you’re more apt to get the support you need, if you offer support back.

What about Nic and I?
So how did we work out his need for a nature sabbatical, plus a desire to work remotely, plus me solo-parenting an active dog, plus honoring my own needs and plans, plus making sure our relationship stays connected? Here’s some of what we came up with:
Nic is supporting my temporary solo dog-parenting by finding a doggy play camp he can attend 3-days a week, so I can work uninterrupted, and get some time to myself.
He's also supporting me by getting a lot of Spring ‘house stuff’ taking care of before he starts his trip.
From my side, I’ll be taking the time to travel to him at different places along this 5-month adventure, so we see each together other every 4-5 weeks.
And we’re both getting creative in between time: Sunday 'coffee dates' via Facetime, cooking dinner 'together' weekly using zoom on our Ipads and him of course sharing his experience by sending me all the amazing photos he'll take in Canada and Alaska! He even bought me one of those digital frames for my desk so he can randomly send me photos. And who knows? Maybe in 2026, we'll make working and traveling on the road a family adventure.
I'm in you corner,
Jen
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