Welcome to the family,

We are so excited at the possibility of working with you and your business. Our goal is to help you increase growth by creating a work smart environment. The goal is not to get more done, but to have less to do. By working with Diligent Assistant, we help you build strategic plans that allow you to navigate through automation and software platforms, ensure your finances are taken care of, hire great people and put out great products and services.

Diligent Assistant provides the support and direction needed to push your business forward in this ever-increasingly complicated entrepreneurial market.  We like to be totally transparent and set standards right from the get-go so we created a welcome kit, allowing you to get a feel for us and the way we work before you sign on as a client!

This Welcome Kit is the best way to introduce you to our team and how we work with our clients. You’ll find in your kit:

  • Our Approach to work
  • Benefits of working with us
  • Getting Started

We’re looking forward to a very successful working relationship. If you have a question at any point, please contact us at grow@diligentassistant.ca

Looking forward to our journey! 

Jackie Appleby

CEO and OBM – Diligent Assistant Inc


Our Approach to Work

Providing value is our main concern and as such we price based on the value you receive, and not on how long it takes us to complete tasks.  We outline your required goals and milestones and set timeframes for completion.

Every client is different and so every service package is built specifically for our clients. Retainers are created for regular reoccurring tasks and projects for one-off software builds and setups.

You’ll notice a huge difference when working with Diligent Assistant over other OBM agencies.


When you buy a package from us, we have made time in our schedules to accommodate your workload. Our commitment to you affects how we work with our other clients. We have also taken time in our consultations to provide you with a package tailored to your needs.

For this reason, we don’t offer refunds on our packages. If you are dissatisfied with our work or relationship, we encourage you to work with us to find mutual resolve.

Time Tracking

The Role of the OBM is one of high trust, strategic planning and collaboration as such, we do not provide time tracking or time reporting to our clients.

We do, however, like to conduct monthly meetings to discuss tasks, goals and deadlines.

Hours of Operation

We work in the Mountain Standard Time Zone from 9am to 5pm, Monday to Friday.

Payment & Invoicing

All retainer package payments and coaching sessions are paid upfront by Credit Card. Direct Deposit and E-transfer can also be arrange for specific circumstances.

Invoices for retainers are sent electronically a few days before the month end, and are due on the 1st day of the new month. All other invoices are due on receipt at the time of issue.

Work will commence once payments are received. Coaching appointments cannot be booked without payment in advance.

For software platform builds a 50% deposit is required to schedule your project and the remaining payments are outlined in your contract.

Sharing Passwords

We take cyber and computer security very seriously. To ensure  safe exchange of passwords and sensitive information, we use LastPass.

Clients are asked to set up an account so that they can securely share their passwords with us. Please share with: jackie@diligentassistant.ca


We understand that time is valuable but sometimes things happen. If you need to change or cancel a scheduled meeting, we require a 24-hour notice.  If you are running late to a meeting, we will try our best to accommodate you, but may need to reschedule if we are already committed to another appointment. As such we will honor our appointments and be on time as well.

Here at Diligent Assistant, communication and collaboration are the keys to success.

We want to continuously improve our processes and services in order to work the most efficiently for us and our clients.

We appreciate regular feedback  and new ideas!

Experienced and Knowledgeable Team

Coming on board with Diligent Assistant means putting yourself in the hands of a very capable and experienced team.

We keep ourselves up-to-date with the lastest industry trends and training where applicable so you can be sure any information we share with you is reliable.

That said, we don’t profess to know everything and if we don’t know the answer to something we will work with you to find a solution.

Turn Around Times

Our days are structured with “chunks” of time allocated to various clients.

Depending on the package you choose, these chunks might be daily or weekly. We rely heavily on our clients to provide us with deadlines within our project management tool, or agreed-upon deadlines during our monthly calls, to ensure that we can deliver in the required time frames.

If you assign us a new task or project outside of our contract scope, we will let you know our availability within 48 hours of receiving the required information. If you make changes to the original task or project, the amount of time required to complete the project is subject to change.

All calls and emails will be returned within 48 hours during business days (Monday to Thursday). That means we will:

  • Respond to e-mail and phone messages as soon as we can, but at most 48 hours from receipt. If we are managing an email box on your behalf, specific response times will be outlined in your retainer package
  • Ask you for feedback, we are not so naive to think that we know everything and you may already be using a system or process that works well
  • Make recommendations and offer solutions
  • Accommodate, where we can, urgent and last minute tasks

Tools and Software

We are happy to work with your PM tool if you’ve already established a routine (i.e. Basecamp, Asana, Trello etc.). We will manage your project on our side with ClickUp. If you do not have a project management tool, we will loop you into our ClickUp system.

Google and Microsoft Suites are our preferred document creation, management and storage systems. We also work with the Adobe Creative Cloud Suite and Canva.

Label With its always a good time to begin

Getting Started

Success for us means understanding your business and needs on a deeper level. Business owners often don’t know what they don’t know, especially regarding Business Operations, Marketing and Sales; this is where we excel.

Your Coaching business may have seen some success already, likely because you are a great coach, but without operational processes and platforms and an all-around entrepreneurial knowledge and mindset, your business can quickly turn into a soul-sucking endeavour.  Our goal is not only for us to get to know your business in its current state so we can make recommendations and provide solutions but also to help you learn and understand all the options for creating a business that you love and where you get to work in your zone of genius.

Getting to know your business is a big job, and we’ve broken it down…


2. The Rise Business Audit, The Shift Your Focus Intensive or the "Nailed it" VIP Intensive

These are our paid consultations spanning 2 hours, 3.5 hours and 5 hours, respectively.

This is where you lay it all on the table and let us know your pain points, your priorities, and your goals in terms of growth and exit strategies (even if you are just getting started) and what your hopes and aspirations are.

We, in turn, will evaluate your needs, your team & projects, and your overall business structure, present solutions and recommendations, including how we can help you going forward.

After your call, within 7-10 business days (we will do a lot of research during this time), you will receive a custom proposal with recommendations and suggestions on packages that could fit your needs. You get to choose whichever one you feel provides the most value for you.

Once you choose a package and sign our contract, we will schedule you into our calendars to get started on your project, coaching or retainer.

If you are coming on board and an OBM retainer client you’ll move on to step 3


1. The Exploration Call

First impressions can make or break a relationship.

The exploration call is the first step in considering if we are a good fit for each other and learning about the key elements of your business and where you need support.

This complimentary 30-minute session will give us a preliminary understanding of your needs and enable a mutual assessment of whether or not we are compatible. Diligent Assistant is known for its “no fluff, no hugs, get it done” approach, which isn’t always a fit for everyone.

Following the outcome of the Exploration call, we could move on to schedule one of our paid consultation sessions that best fits where you are now.

If you haven’t already, Book your free Exploration Call.


3. The Process Development Period (1st 90 Days)

We are now in a relationship.

Communication continues to be at the forefront of this relationship, as we collaborate towards getting you organized and up to speed, and to develop processes and systems that mean you work less in the long run, while doing more business.

During this phase we will identify what can be taken off your plate and eliminated through automation, or refined to become a simpler process. We don’t want to reinvent the wheel so we will also be looking at your existing files and procedures to see where these can be reused.

You will be introduced to other team members who will play supporting roles in your success with their unique skills sets, thus allowing you to get back to the parts of your business that you love best.

This is a time to show us examples of how you operate, what you love and what you hate in deeper detail, and introduce us to staff, if applicable.


4. Moving Forward

Once we have unravelled your knotty ball of wool, we will help create Standard Operating Procedures (SOPs). These are the backbone of your business and allow you to step away and leave things in the capable hands of your well-trained employees and contractors.

SOPs map out exactly how to execute and automate routine tasks. As well as mapping out the process, these SOPs also allow you to consider who the task “belongs to,” helping you to create future roles in your company.

We work using our Coach to CEO Methodology which ensures that your business is growing in a well-supported and balanced manner across all business areas.

The areas are People (Staff, Vendors and Contractors) Sales & Marketing (Getting and keeping customers) Finance (How fiscally responsible is your business?) and Operations (The back-end and beyond). These are all connected together by an optimized mindset that allows you to run your business from a CEO perspective, ensuring that you are making effective business decisions that will fuel your future growth and provide a stabilized business.

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