Effective Deadline Management Will Help You Win and Keep Business

One of the most important aspects of freelance work, specifically for an expert like you, is to negotiate and set reasonable deadlines for each project. Deadlines help you meet client objectives and keep the client’s project on time. Setting a deadline requires understanding the ‘when’ and ‘why’ of an engagement, which allows you to meet the client’s needs, thereby keeping your client happy. In turn, satisfied clients will positively foster and promote your reputation.

Now let’s talk about how to effectively set and manage a deadline.


How do I start to set a deadline?

First, never let your ambitions for quick returns steer you into making poor time estimates. Assess your workload honestly, focusing on your results, not the timeline itself. Sure, it’s admirable to meet a very short timeline, but any zeal should take a backseat to the potential unpleasantness of failing to meet a client’s deadline and needing to ask for an extension. In terms of timeline management, it’s often encouraged to ‘under-promise and over-deliver.’



To this end, try scheduling in reverse. Work backwards by imagining when the final priority will be completed. Think about how the deliverable will appear at this stage. Try to anticipate any challenges you may encounter while meeting the deadline and always feel comfortable asking your client about possible challenges they may foresee.


It never hurts to exercise curiosity, which is why we advise you to ask yourself, and your client, the following questions when negotiating deadlines:

(1) Do you have all the resources you need to complete the task?
(2) Will anyone else be involved in accomplishing the goal?
(3) How long has it taken you to complete similar projects in the past?


Big deadlines might be daunting, but they can be managed.

Make sure the agreed-upon timeline is expressed in written form so you and the client can refer to it throughout the course of the project. And remember, timelines are usually negotiable. Just because the deadline has been written down doesn’t mean it can’t be modified in the future.

Once you’ve agreed on a deadline, identify key milestones that must be met on the path toward the end goal. Break the activities needed to meet your milestones into discrete tasks. Estimate the time and effort each task will demand, while at the same time planning what you can tackle. Form a project plan by putting all the tasks, activities, milestones, and deadlines together.


I’ve negotiated and set a deadline. How do I keep it?

Prioritize tasks with a ‘why?’ included. Consider the client’s needs and their criteria for prioritizing certain aspects or steps within the project. Manage and regularly update a master “To-Do” list in an electronic format, which you can also use to adjust priorities in response to changes in the client’s requirements. Maintain one “To-Do” list version for yourself and another to share with the client as part of weekly progress updates. At the minimum, weekly updates should include tasks completed last week, highlights of your current findings, tasks to be completed the following week, and progress compared to the schedule.

Embrace flexibility. Deadlines and priorities can adjust in accordance with client needs and requests. The scope of work might increase or decrease, a project may get cancelled, or other activities and projects can end up taking more prominence. Be prepared to shift gears as smoothly as possible, especially under time duress and constraints. Update your list of priorities as often as needed based on shifting requirements and the work you’ve already done. Be sure your list includes specific due dates for each sub-task. With each adjustment, share with your client how the changes may affect the project’s schedule and deadline.

When building out your schedule, make sure to incorporate extra time to act as a cushion for possible delays. You can employ ‘task inflation’ to estimate a 20-25% increase in your projected time investment to allow for sufficient. When you can, build into your schedule time for revisions, such as smaller deadlines for initial and adjusted drafts. Plan to tackle similar tasks together.



How should I navigate juggling multiple consulting engagements?

When juggling multiple consulting engagements, allocate time on your calendar for the specific projects at hand, especially as other projects and clients may take precedence. Set reminders for deadlines and share those reminders with stakeholders when applicable.




Regular updates create peace of mind and prevent undesirable surprises.

A critical component for getting along with your client, and any other stakeholder, is to maintain regular communication, including status updates pertaining to the deadline in question. Provide regular updates to stakeholders on tasks in progress, tasks completed, upcoming priorities,
challenges, solutions, and feedback. Address any questions raised to ensure that all parties are on the same page regarding expectations.

Regularly scheduled check-ins can prove helpful in this area. And you can easily schedule them in the form your client prefers. Updates can be provided via:

• Weekly status update reports
• Emails
• Telephone conversations
• Text messages
• Instant messages
• Summary progress reports
• Detailed progress reports
• Site visits

Status updates can offer the client peace of mind once they know the project is progressing at regular intervals. When using these methods to interface with your client, remain open-minded to suggestions and feedback.

Remember that your client is on their own timeline, so tension may arise on their end — through no fault of your own — as internal deadlines approach within their organization. You can help keep the project running smoothly, and earn additional trust from your client, by keeping calm
and remaining flexible in these scenarios.


What about when the project is wrapped up?

When wrapping up the project, remember to ‘run the brakes’ and stop working when you have met the client’s need. Never exceed the client’s budget by solving problems they didn’t request— no matter how apt your expertise may be for that area. Additionally, after wrapping, conduct postmortems. Postmortems are great for exploring lessons learned which may help to improve the next project. During postmortems, you should ask the client the following:

1) What went well?
2) What didn’t go well?
3) What can I do better next time?


What if I can’t meet a deadline?

While it’s not ideal, this does happen. Remember to be transparent. Transparency helps your own stress level and your relationship with the client. Exercise ownership if the missed deadline is your responsibility. And if you don’t know what went wrong, ask the client to help you
understand. Additionally, don’t place blame, exercise honesty, and give as much notice as possible.

Finally, keep track of why your deadlines are missed and arm yourself with that reasoning when tackling future time-sensitive engagements. Should emergency priorities arise, renegotiate an extension for existing deadlines to accommodate the client’s new need. Most of deadline failures are direct results of unsuccessful or incomplete communication between expert and client. Make sure you understand the requirements of a task and how to conduct the work in accordance with your client’s timeline by communicating clearly and asking questions.


“Communication is the solvent of all problems.” – Peter Shepherd

Clear and regular communication avoids and solves problems. Should you encounter a problem that threatens the achievement of the agreed upon time frame, inform your client as soon as possible. Be sure to provide a solution — not just the initial problem — during that communication. Relay priorities on what needs to be done first.

Good luck with your consulting engagements!

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What did you think of this article? Let us know. Feel free to share with us what you liked and didn’t like, how we can improve, and future topics you would like to see covered. We’re more than open to your suggestions!
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