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#SalesQuestions - Why is now the right time?

Liston Witherill
Liston Witherill
19 min read

There’s no way to overcome selling to the right person at the wrong time.

Timing — like so many other aspects of buyer qualification — is a critical component of your sales process.

But how do you know if now is the right time? It’s not difficult to find out. And in this article, I’ll give you a method, specific questions to ask, and a strategy to determine just how motivated your client is.

In music and in life, timing is everything.

Timing is everything in music.

It’s the timing that determines rhythm. It’s the timing that determines how much you’ll like the song, and whether the song “makes sense” to you.

A few slight changes in timing and the song feels different.

Life is just as affected by timing. Without the right (and wrong) timing, my wife and I wouldn’t be together now.

We met in graduate school at U.C. Santa Barbara. I had a girlfriend at the time, and she was newly single. A year and a half later, I was single and she had a boyfriend. It appeared that timing wasn’t on our side.

Just a week before graduation we started dating. She told me that she was going to move back home to Northern California, that she couldn’t stay in Santa Barbara. I suggested she stay in Santa Barbara, and that we live together.

Now, I’m normally a calculating, analytical kind of person. But there was something special about her, and something pressing about the timing. The circumstances meant that we had to give this a shot, even if it appeared impulsive on the surface. The timing gave us the motivation to move quickly and act differently than either of us had in the past — It was the only way we could give our relationship a shot.

It worked. As I write this, we’ve been married for five and a half years.

I’ve made plenty of decisions that didn’t work out quite so well because the timing wasn’t right. And that’s the larger point:

Timing is neutral.

It can work in your favor, and it can work against you. The skill is in figuring out the difference.

When it comes to sales, pursuing opportunities without timing working in your favor can cause the deal to disintegrate right around the time you think it should turn into business. But when the timing is right, it provides motivation for people to act quickly and decisively, just as my wife and I did.

But there’s one wrinkle in the story: When you’re working with a client, they may not know if the timing is right or not.

It’s your job to help them out.

Why we can get the timing so wrong.

So what causes us to sometimes get the timing so wrong?

Sometimes it’s our own failure to ask and properly understand. Sometimes we have to read between the lines to understand the context rather than simply the content of what our clients say. And other times, we need to rely on identifying patterns we’ve observed from past clients.

But sometimes our clients just don’t understand whether the timing is right for them. There are two reasons for this: 1) They know less about your solution and the proper timing of it than you do; and, 2) they may not have full visibility into their organization and, therefore, don’t understand the bigger picture of change occurring within the organization.

Either way, we can help them better understand their own situation and timing by asking better questions.

Timing tells us much more than “when.”

“Why is now the right time to do this project?”

Your clients’ response to this question will tell you much more than simply when or if your clients are likely to buy.

When your clients answer the timing question, their answer may include information about their buying process and motivation to proceed. You’ll also learn about the overall timing of the project and the likelihood that it’ll succeed. So for instance, if you typically find projects most successful within the first 6 months of someone taking a new leadership position, it would be reassuring to discover that your client is still within that window. These internal and external events are called “buying triggers” and factor heavily into the appropriateness of your project’s timing.

Asking about timing may also reveal the larger business strategy at work. As in, what long term value can you provide to your client? What additional projects or ideas can you bring to bear that will help your client succeed? Perhaps more importantly, if your project is related to a seismic shift at the organizational level, you’ll have strong leverage over the sales process and connect your solution directly to the larger initiative.

This simple question may also help you estimate. Depending on what your client volunteers, you may learn important information about the likelihood of executing the project. Is it a priority, or not? You may also learn useful information about the complexity of the deal, and the likelihood of getting it done. If your timing question reveals a large steering committee with 12 people, your sale may be doomed from the outset.

Most importantly, your “why is now the right time?” question asks your client to justify the project and timing to you. This turns the tables in the sales process and asks your client to supply concrete reasons for why they should do the project now. Whatever reasons they state can be used as key selling points as you move through the sale with them.

Quick aside: A related question you can ask is “Why me / us?” This question should be used primarily in inbound (as opposed to outbound) opportunities because your potential client has come to you. This why question will once again ask your clients to describe why they were attracted to your company, what they perceive your differentiators to be, and why those differentiators are especially important to them.

The psychology of “why” will work in your favor.

Any time you ask a why question, the other person will almost certainly answer using the word “because.” What follows “because” is typically a rationalization or justification.

That is, asking why implicity begs the listener to assign cause and effect.

If you ask someone why they saw a movie, they’ll say it’s because they like the actors, director, or maybe because they were curious.

Many of us aren’t well-equipped to assign cause and effect in complicated situations. When it comes to asking your clients about cause and effect, they may not have a good answer for you. But, they’ll definitely have an answer — It just may not be accurate.

And therein lies the issue: Asking a why question will get your client to give a rational answer, but it may be an assumption rather than a truth. But that’s okay. As long as your clients answer the question, you at least know what they think is the reason why now is the right time to buy. Digging a bit deeper may uncover the real reason, and that will come as you continue to dig deeper.

There are only four possible responses to the question.

When you ask “why is now the right time,” there are only four ways your client can answer.

They know why now is the right time. This is ideal, of course, and you should listen intently as they speak. If they can articulate why and you’re satisfied with the answer, you’ll have valuable information that’ll help you and your client as you proceed with the sale.

They don’t know. Your clients knows they don’t have the full picture and they’re willing to say it. Perhaps they were told by a superior to do some research. Perhaps they understand a narrow part of a much larger initiative. Either way, you’ll have to keep digging.

They know, but they won’t share. This is the worst of all situations. If your client is closed off and guarded, take a step back and explain to them why it’s important for them to exchange information with you. There’s no way to help them solve problems if you don’t understand the full context of their situation. If they continue with an adversarial posture, it’s time to call it out and ask if they’d be willing to be more open. If not, you’re in a dysfunctional relationship.

They think they know, but their picture is incomplete. The way to verify that this is the case is by talking to other people within the organization.

You know you’ve heard enough when…

Assuming your clients are forthcoming with an answer when you ask, you might be wondering when you’ve heard enough. The answer is simple: When you can identify concrete reasons for why the timing is right.

If your client replies, “We’ve been wanting to do this for a while,” that’s not enough. If, on the other hand, you learn something concrete like, “It’s part of our company’s annual planning and we finally have the bandwidth to tackle it,” then you’ve heard a strong answer.

Whenever I get an answer like that, I’m curious why they haven’t already done it. Why is this year the right year? Why do you have the luxury and budget now, while you didn’t before? Is it some new information, a new board member… What is it?

There should be some tangible internal or external pressure. That’s the motivation to do the project, and that’s something you’ll tie into your sales proposal.

Part of this process — part of every step of the sales process — is to find out if this is a good fit. It may not be! That’s okay. Maybe the answer is you shouldn’t pursue a particular opportunity after all.

Expect that that will happen, and accept it.

Taking action on the question, and a few follow up questions to ask.

When it comes right down to it, all you have to do is begin asking the question, “Why is now the right time?”

Put it into your own words so it feels natural. The heart of the question is quite simple, and the answers your clients provide can be rich with context.

There are several follow up questions you can ask, depending on how your clients respond:

  • What happened at your company that made this a priority right now?
  • Why haven’t you already done this?
  • Does everyone agree that now’s the right time?
  • What would happen if we did nothing?
  • Why are you talking to me? Why do you think I’m the right person/company for this?
  • Who else agrees that now is a perfect time? How can we get them more involved?

No matter how you ask the questions, just start. What you’ll find is rich information that’ll help you better understand your clients, their pains, and the inner workings of their company.

Want more ideas for sales questions to ask?

Check out the entire #SalesQuestions podcast series:

#SalesQuestions – What’s going on?
#SalesQuestions – How long has this been happening?
#SalesQuestions – When did you notice this was a problem?
#SalesQuestions – What have you done to fix it?
#SalesQuestions: Who else is this affecting?

For more information on remote selling and a complete list of links mentioned in this podcast, visit this remote selling article on our website.

#SalesQuestions – Why is now the right time?:

Full Transcript

Groceries delivered to your front door in 30 minutes. How do they do it? With tons of infrastructure. There are distribution centers and delivery drivers and countless servers to manage a flood of orders. You can go order right now and it doesn’t make a difference if you order from Instacart, Amazon Fresh or your local supermarket. But not one of those companies was first to grocery delivery, not even close.

You see way back in 1996 a startup called Web Van tried to do it. Besides having a terrible name, Web Van made a few mistakes along the way. Of course, they tried this at height of the .com boom, which meant they had lots of money without a strong business model. But their fatal sin? Timing. They were too early. The tech wasn’t quite there yet. The infrastructure wasn’t there and consumer preferences weren’t there either. There just weren’t enough people who were ready to order groceries online yet. There are lots of companies that deliver groceries now, probably even your local supermarket. And why? Because grocery delivery is a pretty good idea. But good ideas alone aren’t enough to succeed. Timing is a big factor too. When you’re selling to a client, you’ve probably identified a project that would be a good idea to do, but is the timing right? Are they ready to buy? In today’s episode, I’ll cover the one question you can ask to find out if the timing is right, reveal more about your client’s motivation and identify concrete next steps to keep the sale moving forward.

Welcome to Modern Sales, a podcast for entrepreneurs, business owners, and sales people looking to have more and better conversations with your perfect clients. You’ll get a healthy scoop of psychology, behavioral economics and sales studies to help you create win-win relationships. I’m your host, Liston Witherill, and I’m pleased to welcome you to Modern Sales.

This is the #SalesQuestions series on Modern Sales where we’re talking about the six questions to ask early in every single sale. In today’s episode, we’ll be covering the question why is now the right time? Each of the episodes in this series have #SalesQuestions at the beginning of the title to help you find them quickly. This is episode number six of six. If you’d like to start from the beginning, just scroll back in your feed. The question I cover in this episode, along with all of the other questions in the series, should be asked in the early stages of the sale. And before we dig into the episode today, a quick read from me, the sponsor of this episode, and my company Serve Don’t Sell.

If you’d like to help your team dig deeper, sell business outcomes and get rid of costly lost deals or price negotiations, I can help you with remote and onsite training options as well as sales consulting. All you have to do is head over to and learn more about how it works. And now for today’s question.

Timing is everything in music. You may not know this about me, but I am a huge fan of music. In fact, I’ve put together mixed tapes for my friends every single year for the last 10 years and I send out the music that I love the most. I produce music, I’ve made my own music, I’ve performed music. And one thing that’s true about music is timing is so critical. One small change in the timing of one particular instrument, one particular note or little hit, it can make the whole song sound different and in that way timing is kind of a funny thing.

I met my wife in grad school but we never dated until the very last week of school. We met each other on orientation day and then almost two years later we dated for the very first time that last week of school. You know, our timing wasn’t right. When we first met, I had a girlfriend and then she had a boyfriend and then we had just a week left until we both graduated and she was moving back home with her parents. I was not willing to let this happen without offering some alternative and so after a week of dating I did offer an alternative. “Let’s move in together.” I told her. Sure it was bold and there was a lot at stake, but there was another pressure too and that was timing. While timing didn’t work in favor of Web Van, my wife and I are still pretty happily married despite what may seem like an impulsive start and this is all to say that timing is neutral. Sometimes it works in our favor and other times it doesn’t. The skill, of course, is being able to tell the difference. And that’s what we want. Because the alternative is working hard on an opportunity for months only to have it disintegrate at the end because the timing was never right. But when the timing is right, it provides motivation for people to act quickly and decisively just as my wife and I did.

But there’s another problem too. Your client may not know exactly when the timing is right or why. Again, more good news, you can help them understand. Now what causes us to get the timing wrong is that sometimes priorities change. The timing was right in the beginning. The timing no longer works as we move through the course of the sale. And as sales take longer, as you charge more, as the things you sell are more complicated, they’re going to take longer, the more likely we are to see priorities change. Sometimes our client doesn’t have full visibility into their own organization. Maybe the bigger story in the organization is way above their seniority level, so they genuinely don’t know what’s going on with the timing. Well that’s okay, but this is a situation where we might get blindsided.

This is also a sign that we’re not talking to the right people. We want to know, at least have an understanding, of what’s going on within the organization so that we can tie our project back to the greater goals of the organization. And of course sometimes clients just don’t want to tell us. Now here’s the thing about that, I prefer not to be in these kinds of relationships. I give away a lot of free and inexpensive advice and products, case in point, what you’re listening to right now, so I tend to point people in that direction if they’re not willing to be forthcoming with me. You may hear this and think that that’s a luxury and in some ways it is, but I’ve also worked really hard to be able to produce all of this content so that people can understand who I am and know that they can trust me, and if they don’t trust me, I’d rather not do business with them.

The solution to this timing conundrum is to start asking your client about their timing. Asking them about timing will provide immense insight into your client’s buying process and motivation. It’ll tell you a lot more about the overall timing of the project and the likelihood that it’ll succeed. It will also tell you a ton about follow on opportunities to continue working with your client beyond the initial sale, as in, what longterm value can you provide to your client? How is the timing of their purchase part of a larger change story? And the best way to find all of this out is to ask this one question, “Why is now the right time?” In my experience, most people will just answer you without hesitation. If your client is guarded whatsoever, just take a second to explain to them why timing is critical. And towards the end of the podcast, I’ll give you some other examples of questions that you can ask if this one doesn’t land for them.

Now, the goal of asking this question is to determine the larger initiatives going on at the company. So if you’re, say, selling marketing consulting and someone is asking you for a new website or a new video campaign or some complicated online funnel, whatever, it doesn’t really matter, what you want to know is, “Why is now the time to do that? What else is going on at your company that’s requiring this to happen and how will this benefit all of your greater goals?” That’s what we want to know, and we want to understand any buying triggers that’ll help the project along. So if someone is new to their role at a company that’s a strong buying trigger, right? They may say, “Well, I’ve only been here for three months or six months and I really want to implement this new plan and I need your help in doing it.” Okay, great, right? That is a strong motivation, a strong buying trigger. There’s lots of other buying triggers that I mentioned on the podcast before, but basically if you look back at when clients buy and why, what you’ll start to see emerge are patterns in what causes people to buy or what other external or internal events are happening that are causing them to buy and we want to look at what those are.

When we ask about timing, it’s also going to help us estimate the complexity of the project and getting the deal done. It’ll help your client justify to you why they should do the project as well and let me explain this. Whenever you ask a “Why” question of your client, this isn’t a typical sales question that most people will ask. Some of us of course are asking it already, but when you ask a client why they will respond with the word, “Because.” They will start to rationalize or justify why now is the right time to buy. This is important because if they have a strong answer, not only will you have more insight into their buying process, but they’ll be making the case for you about why they should buy right now, which you can repeat later when you present your pitch for working together. And of course there’s another question you can ask why they think you’re a good fit for the project. So not just why is this the right time, but also, “Why am I the right fit? Why are you talking to me? Why are you talking to my company?”

Now there’s a small caveat on that question and that’s that this should really be used primarily on inbound opportunities since they’ve chosen you. If someone comes to you, it’s a lot easier to ask this question, but it’s going to get your client to articulate what they like about you, what they think is different about you, what’s attracted them to you and your company. They’ll tell you about what they perceive your differentiators to be and why those differentiators are especially important to them. And I mean, you want that kind of information, don’t you? So that’s a variation of this “Why” question. One can be around timing. One can be around why you’re the right fit.

Now let’s talk about psychology, shall we? When we ask, “Why is now the right time?” Your client will likely begin their answer with the word, “Because.” And that’s because we’re trained to give rational answers whenever we’re presented with “Why” questions. And that’s because “Why” questions implicitly ask people to identify cause and effect. That’s the reason for the “Why? Because.” orientation. So when we ask a “Why” question, someone answers with, “Well because…” Insert the blank. Here’s one of the challenges with that. We want to know the cause and effect here. But the problem is that a lot of people just aren’t that good at understanding cause and effect. So if your client struggles to answer the “Why” question, there are a few fallbacks you can ask to help them create the cause and effect association. For now it’s enough to get them to think about the cause and effect. That’s the psychology behind the question and that’s what we want our client to do.

Now when you ask the question, there could be a few different answers you might hear from your client. First one, of course, they know why now is the right time, they can articulate it to you, you’re satisfied with the answer, and you can make a judgment about how aggressively you want to pursue the opportunity because you get a sense of how deep their motivation is. Secondly, maybe they just don’t know and there’s two variations of they don’t know. One is they know they don’t have the full picture and they’re willing to say it and secondly, they don’t know what they don’t know. So if that’s the case, when we ask, “Why is now the right time?” And if they say, “I don’t know.” Then I’d follow up with a question like, “What other information would we have to find out? Or who else might we need to talk to in order to get a clear picture here?” And they’ll probably know the answer to that question or at least have some inkling.

Another answer you might hear is that they know, but they won’t share. They’re guarded because they’re treating the relationship as adversarial. Why? Why are they doing that? I would want to dig into this. Maybe it’s a matter of trust. They don’t trust me yet or they don’t trust you yet. Maybe it’s that they’ve been burned in the past and wouldn’t we like to know that? Whatever it is, we want to know why they’re being guarded. Next, perhaps our clients think they know why now is the right time, but their picture is incomplete. The way to verify this is by talking to other people within the organization. If something doesn’t add up, the reason is too strong or not strong enough, then you’re going to want to continue to do some homework and talk to other people within the organization. All of this begs the question when you ask the question, “Why is now the right time?”, “How do you know when you’ve heard enough?”

Well, when you can identify concrete reasons for why the timing is right, that’s essentially what we’re going for. If they say something like, “Well, we’ve been wanting to do this for a while and now it’s finally the right time.” To me, that’s not enough. Because if they’d been wanting to do it for a while, why didn’t you do it six months ago? Why didn’t you do it a year ago? Why didn’t you do it two years ago? Why do you have the luxury now? Is it budget? Is it personnel? Is it bandwidth? Is it new leadership? Is it skills? Is it a job change? What is it? And you know you’ve heard enough if you have an understanding of where the internal or external pressure is for this project. And look, part of this process, part of every step of the sales process, is to find out if this is a good fit. It might not be. That’s okay. Maybe the answer is you shouldn’t pursue this particular opportunity. We expect that that will happen some percentage of the time and we must accept it as hard as that might be.

So with all of that said, here’s how I want you to take action on this question. Just start by asking the simple, very basic question, “Why is now the right time?” Some alternatives or follow up questions you can ask are, “What happened at your company that made this a priority right now? Why haven’t you already done this? Does everyone agree that now is the right time?” One that I particularly like, “What would happen if we did nothing? Why are you talking to me? Why do you think I’m the right fit for this?” And finally, “Who else agrees that now is the perfect time? How can we get them more involved?” Ultimately we want to help our client not only understand if now is the right time, but if it is we want to help them get through the sales process as quickly as possible so we can start to solve those problems that our client needs help with.

That’s it for this episode of the #SalesQuestions series. This of course is the last episode in the series. Next week I’ll be starting a brand new series called #SellersBecomeMarketers where I explore the convergence of sales and marketing, the lessons marketing can teach us about selling and the core marketing skills all salespeople need to succeed in modern sales including and starting with that one single drastic change that’s led to all of this.

Now, if you aren’t already subscribed to this podcast, please do so by clicking the subscribe button in iTunes, Spotify, or wherever you listen. You can also get notified of all podcast episodes with some behind the scenes info as well as other exclusive sales content I put out by signing up for my email newsletter at It’s totally free and it’s linked in the show notes. And finally, if you’re looking for help training your team to sell more of your big hairy complicated products and services to big companies, I can help with remote and onsite training options. I can help them all have better, more meaningful and more value driven conversations. Just head over to, click the contact button and you can fill out a quick form to begin the conversation. Thanks so much for listening. I’m Liston Witherill of Serve Don’t Sell, and I hope you have a fantastic day.

Modern Sales Podcast