How To Finally Overcome Your Problems Meeting Deadlines

Recently I was in a conversation about problems meeting deadlines with a group of Service Providers.

I really think it should have been about problems missing deadlines because nearly everybody was frustrated that they were consistently not meeting deadlines, they themselves had set.

Apparently, encouraged by my silence, someone said to me, “you very quiet…you know how to meet deadlines?

Yes, I do! And I meet them most of the time, too! I answered enthusiastically.

Oh! I forgot you’re the self-development expert! You know something the rest of us don’t know?! We would love to hear!

Sarcasm aside, there are several reasons why meeting deadlines is important to service providers, but first let’s be clear what’s a deadline…

What is a deadline?

On the surface, we can think of a deadline as a specific date or time by which a task, project, or obligation must be completed. In other words, it represents the final moment when something is due, after which it would be considered late or overdue.

In business it’s more than that. It’s a goal you set for yourself, the start of a relationship built on trust and how you organise your work to achieve these.

In other words, they represent a yardstick by which you determine when certain tasks need to be completed and how much time is available to complete them. 

The effectiveness of deadlines often depends on them being realistic, clearly communicated, and having meaningful consequences tied to meeting or missing them.

Why Meeting Deadlines Is Important for Service Providers

Generally, there are many reasons why meeting deadlines is important.

But if you’re a service provider, here are reasons you should want to meet deadlines:

1. Competitive advantage – In markets or niches where service quality is relatively similar, reliability often becomes the key differentiator. Clients will often choose a service provider who consistently delivers on time over one with slightly better quality but less reliable timing.

2. Trust and Credibility – When you consistently meet deadlines, clients develop confidence in your reliability. This trust becomes the foundation of long-term business relationships and often lead to them recommending your services to others.

3. Professional Reputation – In industries which depend on services, word of mouth is the key form of marketing. If you earn yourself a reputation for consistently missing deadline, this will spread equally fast. This will seriously impact your ability to win new business and retain existing clients.

4. Cash Flow Management – You are very aware that how (and if) you get paid is tied into agreements with specific delivery dates. Missing deadlines can delay payments, affecting your cash flow and your ability to manage your own business operations effectively.

5. Avoid Creating Domino Effects For Clients – Your clients typically build their own timelines around your delivery dates. When you miss deadlines, it can create a domino effect that disrupts their operations, marketing launches, or other critical business activities. This ripple effect can be costly and damaging to their business. And yours  as well. 

Strategies To Overcome Problems Meeting Deadlines

There are several “text book” reasons why you and most other service providers have problems meeting deadlines.

I know those reasons well having worked as a Project Officer for a regional (Caribbean) organisation and a European-based one with global reach.

But Scope creep, unclear requirements, resource allocation issues and technical complexities are not quite your problems.

Keeping it real, your problems are more personal and to do with you, rather than from any external source.

How do I know?

For more than 25 years, I have been a service provider providing consulting, coaching and training services to small business owners, other service providers and entrepreneurs.

So I’m sharing with you 7 key challenges that I discovered service providers have with meeting deadlines and the strategies used to overcome them.

1. Change the way you think of deadlines

When you have several deadlines to meet, especially if you work alone, you experience a feeling of overwhelm.

Yeah…it feels like deadlines are threatening your life and really breathes new life into the definition as researched by Robert Charles Lee.

So what if you could think of your deadlines as timelines, instead?

A timeline feels like something you can achieve while saving your own life. It creates a mental picture of being in control, meeting targets repeatedly and holding yourself accountable.

So why not make one of your secrets to meeting deadlines thinking of them as “timelines?” 

Yes…it’s all in the mind but isn’t that where everything starts?

2. Remember: A deadline cannot exist in a vacuum

I am amused when people try to live their lives in silos.

You want to leave your “home problems” at the door when you enter work and you leave your “work problems” at the door when you get home.

Really? Try that when work and home are in the same location…

Just imagine: you’re caring for your sick mother, your son just lost $50,000 in his business and your partner is having a midlife crisis.

I don’t know about you, but that’s enough to kill my feelings for working, far less for meeting deadlines. 

So if you’re one of those people who believe that you can be productive 100% of the time, regardless of your personal issues, congratulations!

For the rest of  you, understand that your life is made up of many parts.

Therefore, to meet deadlines consistently, you must consider all parts of that life when you make them. 

Stated more bluntly, meeting deadlines cannot exist in a vacuum.

3. Pay attention to your energy levels

If I know you, you lead a high-stressed lifestyle, as most small business owners do… going, going from morning until night.

And when you’re already tired and have one or more deadline to meet, you will have problems meeting deadlines…fuh real. 

On the other hand, what if you live a harmonious life?  You eat well, make time for exercise and support all this with “me time.”

In this scenario, your energy levels are consistently high.

It follows then, that your capacity to meet deadlines will be higher, if your energy levels are consistently high.

So try to bring some balance in your life – physical, mental, emotional and spiritual. In this way, the energy will be already there. Therefore, to achieve a timeline, all you need will be a shift in priorities.

4. Accept that how soon after a proposal you get the job matters

Are you familiar with this? I am…

You meet a potential client. The meeting goes very well. You send them the requested proposal. And on time. Then the time you set for a response comes and goes and you cannot hear from them.

After several attempts to follow-up, including using advice from Oren Klaff, you give up. And then it happens.

One afternoon, some weeks later, out of the clear blue sky, you get a call from the business.

They are calling because the problem they are experiencing, predictably has worsened, and now they want to know how soon you can start for them.

No Problem. But they still want you to complete the project by the date you had originally proposed.

Seriously? And when you review the proposal, it now seems as foreign to you as the Magna Carta.

Taking on the pressure of meeting deadlines under these circumstances are often only attempted because of the situation discussed in #7 below.

5. Acknowledge your feelings for the client 

Do you feel the same way about working for each of your clients?

Don’t lie to me now. You have some clients you like working for better than others. I do…we all do. It’s part of being human. It’s also part of the work we do and why we might have problems meeting deadlines.

Listen, when I was a child, my Mom used to make cushion covers to supplement her income. What always stuck with me was how she used to complain about certain customers.

I remember her complaints because she claimed that how fast she was able to make a set of cushions was dependent on how miserable or accommodating the customer was.

Lord knows that many years later, my ease in meeting deadlines or timelines swings around on similar factors as my mother’s. The only difference is that I know it comes from me and not the client. 

When you like working for a client, it seems that precious little can go wrong when you’re working on their projects. Even if something goes wrong, fixing it is also a breeze.

When I have to work for a difficult client, I admit I have to dig deep in my professional bag, to save my human nature from winning.

As you can imagine, that makes achieving any timeline, all the more difficult.

When you have such a client on your list, be sure to add some extra time to any projected date you give them for the completion of their project.

6. Allow for learning needs  

A few years ago, I was the Capacity Building Consultant on an IDB-sponsored project for a small organisation in the agriculture sector.

I have a strong background in the not-for-profit sector, especially in the capacity building niche, hence my selection.

On the other hand, apart from planting some pawpaw seeds and having the giant African snails eat the plants as soon as they were 0.7 inches tall, my background in agriculture was almost non-existent.

In designing a work plan for this project, I factored in the time I would need to learn the various aspects of the agriculture industry, relevant to the project. This was to help me meet the deadlines without pressure and…you just don’t mess with IDB.

When you have not done a particular type of work before, or if you have not worked in a certain sector, please include learning time in any deadline you set.

If you don’t, meeting deadlines on such a project will be challenging. If you meet them at all. 

7. Accept that your bank balance matters to your meeting your deadlines

I don’t know about you, but I work for money.

Yes…I donate my services to deserving organisations, but I can only do this because I get paid for other services I deliver.

Now, even with my best effort, there are times when my available cash dips below my ideal balance.

In times like these, even though I have to call up my incredible will power and massive amounts of energy, I meet any timelines I set. I don’t negotiate with myself. 

On the other hand, when I have a healthy balance on my checkbook, I feel I can buy just a little, little bit of procrastination.

You know what I’m talking about…don’t you?

So accept that at some level, how badly you need the money will impact how you set deadlines and how well you meet them.

If you can honestly consider this when you make a work plan for a project, you will set better timelines that will keep your professional reputation intact.

How to push the reset button on meeting deadlines…

Now that you know 7 ways in which you get in your own way of setting deadlines, you will want to rethink how you set and meet them. 

So I want to make that easy for you.

The next time you have to set a deadline, forget all you know about project management and ask yourself the  following questions: 

 1.  Am I setting a deadline or a timeline?

2.  How can I get the energy I will need?

3.  What is happening in my life that could prevent me from meeting my deadline?

4.  What do I have to re-learn about implementing this project

5.  How can I prevent my feelings for this client getting in my way?

6.  Have I done this type of work before?

7.  How can I stop my bank balance from being a factor in this deadline?

When you answer these questions honestly, you will find that you can easily transform the problem of meeting deadlines into the pleasure of achieving timelines. 

To your meeting deadlines success…