The Power of a People-First Approach: Winnipeg Police Association and TDS

The strongest relationships are those built on integrity and respect, and perhaps in no other sector are these traits more highly valued than law enforcement, law and labour organizations.

published 02/27/2024

TDS and the Winnipeg Police Association place trust at the forefront to deliver human outcomes

The strongest relationships are those built on integrity and respect, and perhaps in no other sector are these traits more highly valued than law enforcement, law and labour organizations. TDS and the Winnipeg Police Association (WPA) embody the benefits and strength that can come when two community leaders prioritize humanity. 

“There's always case law that develops across the country, and things do change in labour law as well,” says Cory Wiles, President of the WPA. “TDS is a leader in the community as far as labour law goes.”

The Winnipeg Police Association has been representing civil servants and police officers for well over 100 years. They began operations in 1918, and today they are the bargaining agent for over 1,400 police officers and approximately 550 civilian support staff. They work with the Canadian and Manitoba Police Associations, lobbying for positive changes in law and labour working environments and for safer communities.

Roots that run 135 years deep

TDS, with roots that run more than 135 years deep in Manitoba, has long been a source of legal service and support to the WPA.

“If there's an in-house labour issue and internal rules and regulations violation, a complaint, or negotiations, TDS will help us handle it and deal with our professional standards unit as well as IIU,” says Cory, “they offer insight on day-to-day and specific issues.”

Leading the way for TDS in this relationship is Keith LaBossiere, who, in addition to serving as the CEO and Managing Partner of the firm, has significant experience with police employment law and public sector labour relations. This includes providing advice and advocacy as well as being frequently involved in negotiating and litigating such matters.

Working with TDS, though, means that you have access to more than just one legal expert—you are working with a team that is committed to and practices collaboration. It is this bench strength that allows TDS to offer in-depth and valuable advice that is specific to WPA and their unique needs.

Cory states, “We feel that we're getting the best of advice that we could get anywhere.”

Responsive and experienced

Paired closely with this collegial approach is the principle of responsiveness and communication. To respect someone’s time is to respect them. TDS understands that being available plays a major role in building mutual trust. 

“I can honestly text Keith at 10:00 at night and ask him if he's got a second for a phone call because an issue just came up, and he'll make time for us,” continues Cory. “He’ll even come down and make himself available on short notice for the members themselves.”

These issues that the Winnipeg Police Association face on a day-to-day basis are often unique even within the labour and employment sector.

“It weighs extremely heavy on our members both at work and at home. The quicker we can get a resolution the better for everyone. The assistance we get from TDS and the way they prioritize us allow us to ensure as speedy a turnaround time as possible.”

The tenure and experience TDS possesses in their service areas aid in efficiency. Their longstanding relationships with many community and labour organizations, including over 30 years of partnering with the WPA, afford them unparalleled insight upon which they can draw.

“There's a huge level of confidence that we have in them because our relationship was built over time. They can speak to past cases and agreements that have been made, and for that, we really lean on them. Ours are businesses where trust can be an issue, and the relationship that we've built there with the TDS team is second to none.” explains Cory.

Building and maintaining trust

There’s no substitute for trust. It can be difficult to find and hard to foster, but the benefits that come from taking a human approach to service and problem-solving can yield results that bring value to all involved parties.

TDS and the Winnipeg Police Association are proud to have a relationship steeped in trust. 

“I truly don't know if we're able to do our job and I do my job more specifically in this role without Keith and his crew there at the office.”

DISCLAIMER: This article is presented for informational purposes only. The content does not constitute legal advice or solicitation and does not create a solicitor client relationship. The views expressed are solely the authors’ and should not be attributed to any other party, including Thompson Dorfman Sweatman LLP (TDS), its affiliate companies or its clients. The authors make no guarantees regarding the accuracy or adequacy of the information contained herein or linked to via this article. The authors are not able to provide free legal advice. If you are seeking advice on specific matters, please contact Keith LaBossiere, CEO & Managing Partner at, or 204.934.2587. Please be aware that any unsolicited information sent to the author(s) cannot be considered to be solicitor-client privileged.

While care is taken to ensure the accuracy for the purposes stated, before relying upon these articles, you should seek and be guided by legal advice based on your specific circumstances. We would be pleased to provide you with our assistance on any of the issues raised in these articles.

Meet the Client Team

Keith David LaBossiere, K.C.
(204) 934-2587
Terra Welsh
(204) 934-2383
Miranda Grayson
(204) 934-2423
Kristin M. Kersey
(204) 934-2305
Robert W. Olson
(204) 934-2347

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