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How To Talk About Timelines

Updated: Oct 12, 2022

This article was co-written by Kevin Legg and Stephen Gonzalez.

When most salespeople talk about deal timelines, they ask their prospects: “When can we get this done?” or “Could we complete this transaction by X time?” They probe and probe until they get a workable answer from the client. What they don’t do is understand why that timing works, why it might not work tomorrow and why some alternative timing isn’t better. Satisfaction with this kind of shallow understanding is, unfortunately, a common characteristic of mediocre sales professionals. This article will show you how to avoid the same fate.


Assume you need to buy something expensive for your company and you know that the salesperson you’re working with is measured by how many sales they close this quarter. Do you assume the salesperson would prefer to get the deal done sooner or later? Would they push you, or try to incentivize you, to sign the contract prematurely? And how about you…would you try to slow down the process in order to evaluate all your options, remove emotion from the decision, and doublecheck all the boxes so you don’t regret your decision later?

Most salespeople mistakenly try to shorten sales cycles by trying to control them – with discounts, threats, pleas, bargains, you name it. They’ll do anything, even work against their client, to get the deal done.

Great salespeople, in contrast, first try to understand the client’s timelines and then work together with the client to manage the timelines where it makes sense for both parties – not just for one or the other. These salespeople find that clients are more likely to be transparent about key information, more likely to follow-through on their commitments, and more likely to see the deal through to completion.

So how do you get better at managing timelines? You can get a long way by following 3 simple steps…

Step 1: Discover The Client’s Timelines

Your first job is to identify and organize all of the small amounts of time that go into completing a sale. In order to do that, you’ll need to be able to separate two terms in your mind:

  1. Timing: the choice, judgement, or control of when something should be done. “I want to go-live by August” is statement about timing.

  2. Timeline: a chronological arrangement of events in the order of their occurrence. “We first need to get approval from the CEO then legal and procurement, before we can sign-off” is a statement about timelines.

Understanding why certain timing works for the prospect usually hangs on your ability to understand the timelines that drive it. So how do you better understand your prospect’s timelines? Ask better discovery questions…

High-Yield Discovery Questions: Timeline

The best way to discover timelines is to ask your prospect about them, and the way in which you ask can make all the difference. Try to be unbiased and curious in your tone and avoid seeking only the answers you want to hear, or responding positively or negatively to the answers based on how they benefit you. Channel the style of an investigative journalist – ask a range of questions to uncover hidden details about their timeline and better triangulate information provided by multiple sources.

Here are a few high-yield questions to get you started:

  • How are you thinking about timing for this project?

Starting with a semi-open question like this gives your client the opportunity to share as much (or as little) as they want about the timing and timelines for the project. It’s best not to interrupt. Instead, give them the silence they need to share as much as possible.

  • What would happen if you didn’t meet that timeline? OR Let’s say the project only happens in {3 months after their target date}. No big deal, right?

The point of this question is to test what the client has shared in #1. This will show you how serious they are about the project and for what reasons (need), and they may also reveal other stakeholders or decision-makers when defending their timelines (“It can’t be delayed, the CEO himself is pushing me to get this done this quarter!”)

  • Besides yourself, who else would need to be involved in this?

Once you understand the overall timing of the project, asking this question will give you an understanding (or help you to fill in the gaps in your understanding) of the different components (or “timelines”) that make up the entire timeframe. These timelines may include the time it takes for different departments or stakeholders to weigh on this decision, important events (meetings, holidays, or other milestones) that need to happen before sign-off, other projects that need to completed beforehand, and so on. This question will also provide insight into how much information your prospect is willing to share with you – a potential indicator of your standing in the account or how much trust you’ve built up with that person.

  • For most of our clients, {The Department Head, Legal, Compliance, Board of Directors, etc.} usually want to have a look at the agreement before we sign-off. Is that true for you as well?

This is nearly the exact same question as #3 but is rephrased as a leading question. Clients who appear guarded and try to dodge question #3 are more likely to respond when directly asked about the involvement of specific stakeholder(s).

  • Are there any other constraints – budgetary, manpower-related, other priorities or projects – that have to be resolved before we know this is going to move forward?

This question provides the client with an opportunity to think about what external factors could influence this deal for better or worse. In many cases, the client might mention something that they haven’t previously thought of, which could be a critical new piece of information that needs to be explored further.

Pro-tip: To get your client talking openly and honestly about the timelines of their project, try practicing the virtual close a wonderful concept that we teach to nearly all of our clients.

Bear in mind that not all of these questions need to be asked in the first meeting, and one single person may not even be aware of all of the timelines and boxes to be checked before they purchase your solution. Every situation is different, but it’s important that you’re prepared to ask these questions and to constantly aim to stay up-to-date by continuously challenging and refreshing the information you already have.

Your first job is to identify and organize all of the small amounts of time that go into completing a sale.

Step 2: Contribute Your Own Timelines

It’s important for you to not only ask about timelines, but to also contribute to the conversation. As a salesperson, your organization’s timelines matter just as much as the client’s if you are both working toward the same end-goal, so it’s important that you are both on the same page about what approvals, agreements, documents, etc. you need – and how long each will take to complete – to avoid surprises and delays later on. A statement like…

“Our two key implementation resources are booked solid in the second week of May, so I don’t want to commit to that timing – is it possible to move things forward by 30 days to April – or push them back to June?”

…can signal that you’re eager to please the client, but still principled and practical in how timelines are discussed and organized. Sharing up-front that there are steps and processes that factor into the timelines will help build reciprocal trust. Here's another good example:

"We will do three test-runs of the entire sequence before going live with you. Those require at least 5 days. Do you have enough time to include that?”

Step 3: Manage The Timelines

Now that you understand what the timelines of your deal are, your second job is to manage them. It’s now up to you to create efficiencies that can help you shorten the process. Here are three best practices:

Tip 1: Work tasks simultaneously

Can you simultaneously advance two or more components of a deal? Often there will be opportunities to do so in collaboration with your prospect. One way to achieve this is to invite an additional party to a meeting. For example – if compliance, finance, HR and operations all need to green-light your deal, can you take four separate meetings and reduce them to three, two, or even one?

Another way to achieve this is to delegate team members from your organisation to “match” team members at the prospect organisation to have simultaneous 1-1 engagements on their respective issues. Tech can work with tech while legal works with legal, and sales works with procurement. A word of caution - when using this tactic, communication and alignment are key. It’s important that the sales rep takes a leadership role and makes sure all parties have clear marching orders are working toward the same end-goal.

Tip 2: Eliminate unnecessary steps

Are there steps in your sales process that your client can do without? Can they be eliminated altogether?

Take a personal example - I once “leapfrogged” a lengthy review from a compliance officer at a hedge fund by providing access to the compliance officer from a sister fund who had previously reviewed my firm’s NDA agreement. The fact that a respected peer had put us under the microscope previously effectively removed that step from my sales timeline, and advanced everything by at least one week. We’ve seen similar examples in everything from accepting email confirmations to using e-Signature software to completely cutting out stages of the sales cycle that no longer add as much value to the client as they may have in the past.

Tip 3: Look for opportunities to push the process forward

Any strongman who has pulled a semi-truck will tell you that momentum is your friend. Sales is the same way. You should be constantly asking yourself the following question – is there anything within my control that I can do to help move this opportunity forward?

Stephen once had an opportunity with a bank in Cambodia that required him to get internal certification from a different business unit in his company on his proposed bill of materials to the client. Instead of waiting a month for the formal product certification announcement, he was able to track down the Product Manager in India and get the confirmation he needed well in advance of the formal announcement – shaving a month off his timelines. In my previous role, we developed a practice of asking prospective clients to sign-off on our NDA after the first or second meeting, well ahead of the typical process of waiting until a formal proposal had been accepted. Doing this allowed us to save at least a week of time in the critical final stages of the deal.

The possible tactics that can help you accelerate the timeline of a deal are endless. However, you must always keep in mind that no matter where your creativity leads you, your tactics are best used in collaboration with the client – without arm-twisting, cajoling or sleight of hand.

Bonus: Manage Your Boss

The better you are at understanding and managing timelines, the better you’ll be at sales forecasting. Great sales people know how to manage the expectations of their managers on when deals will close, and great managers know how to see through the façade of a rep who hasn’t done their due diligence.

Until you make a deliberate effort to understand the timelines from your client’s perspective and explore the risks to those timelines and the opportunities to shorten them, you won’t be able to do this confidently. So, if you find that you are regularly closing deals late, or adjusting the close date on deals to accommodate for delays and setbacks then you want to study where those delays come from, and set longer sales close dates, or address those delays directly.


So – find out what your client’s timelines are by starting with high-yield questions and then pursuing with a virtual close, making sure to add your own timelines in along the way to complete the picture. Then, get creative and pursue every opportunity to work together with your client to manage and shorten the timelines of the deal wherever it makes sense for both parties. No trickery, no foolery. Sounds simple enough, right? Then get to it!

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