Internal Operations & City Leadership

I recently asked for a status update on the hiring of Winnipeg’s new Chief Administration Officer (CAO) and would like to share some thoughts with you on this important role. As you may be aware, this past June, the former CAO announced his retirement in February, 2019 and the search for a new CAO was initiated.

In May 2019, Harris Leadership Strategies was selected to assist with the recruitment effort. Council did not meet as a group (Mayor and 15 Councillors) to discuss what qualities we would be looking for in a new CAO. Instead, the Mayor appointed a ‘recruitment committee’ to oversee the recruitment process, and to ultimately recommend the City’s next CAO to Council to vote on for final approval. (Recruitment Committee: Mayor Brian Bowman and Councillors Sherri Rollins (Fort Rouge-East Fort Garry), Matt Allard (St. Boniface), Devi Sharma (Old Kildonan), Ross Eadie (Mynarski). Additionally, the recruitment firm emailed each Councillor nine questions and asked them to respond with comments.

We were not provided a timeline on when the recommendation would come forward, but I would anticipate Council will be voting on a new CAO before the end of 2019.

Job Description: See details of Winnipeg’s CAO job description, ultimately crafted by Harris Leadership Strategies and approved by the Mayor and the recruitment committee. The job description is quite encompassing at first glance.

  • Challenging the organization to be innovative, responsive and accountable to residents;
  • Influencing people to embrace, initiate and sustain positive transformational change, including reassessing service delivery, service priorities and how current human and financial resources are utilized in the organization;
  • Promoting employee engagement by cultivating a safe, supportive high-performance work environment;
  • And the list goes on and on and on!


One of the ‘Key Responsibilities’ listed is: To provide leadership and direction to the organization to promote the effective and efficient delivery of City services.  From my experience now working five years within the City’s bureaucracy, I have to say if the CAO can accomplish one thing – THIS is the key responsibility and deliverable!

These next few comments may appear astounding – but they are factual.

The internal operations of how the City functions are in dire need of a fundamental overhaul.  The level of dysfunction, lack of broad communication and silo based approach makes me question how the City even functions. Clearly it is also causing concern for the Province, as they have now stated they will be conduction a review of certain departments and functions. I admit I have never worked in a large bureaucracy before, with collective agreements, multiple departments, and thousands of staff, though I did work at a company that’s been recognized as one of Canada’s Best Workplaces for 13 consecutive years – and the working environments couldn’t be more opposite.

  • As a Councillor, it’s incredibly difficult to deliver a high level of service to residents when the internal operations of the organization are not working.
  • Under the current Mayoral and Executive Policy leadership, over the past 5 years, we’ve seen:
    • The departure of 6+ senior transportation engineers in top leadership roles from the Public Works department
    • The departure of over half the legal department, including the City’s top solicitor
    • Missed deadlines for filing of legal claims
    • Contempt of court charges being laid against the City of Winnipeg for violating a Court of Queens’ Bench order
    • Complete chaos occurring with staffing accountability in the Property, Planning and Development Department
    • External audits revealing a failure to communicate both within the organization and to the public on capital planning processes (involving multi-million dollar projects), lack of defined roles and job descriptions for staff within departments, lack of criteria that identify files that pose significant risks to the organization (political, financial, etc.)
    • The need to increase the legal departments budget by over a million dollars to hire external legal advice to battle multiple court charges
    • The breakdown of the ‘front line service center – 311’ for the public’s service delivery and inquiries, resulting in Councillors being the ‘311’ operators for the public
    • And there are many more functions – not functioning – that I could cite.

Clearly it is also causing concern for the Province of Manitoba, as they have now stated they will be conduction a review of certain departments and functions.

All of this internal dysfunction leads to an incredible downturn in staff morale, a negative impact on corporate culture, and makes it really difficult to deliver a high level of service. While things may appear all ‘sunshine and happy’ in tweets and Instagram posts, I can assure you – working in this environment is very very challenging, and even more important, the FINANCIAL COST to taxpayers is incredible.

And all of this is happening in a time when Winnipeg’s economy is on an upswing – when the City is growing with more and more people moving to Winnipeg due to very positive immigration policies. The City’s internal operations should be working at an optimal and efficient performance level. I grew up on a farm and the old adage ‘make hay when the sun shines’ couldn’t be more true! The City’s processes, the internal communication and operations should be running ever so smoothly to MAXIMIZE on the very positive growth potentials in front of us – but they’re not. Because the internal workings of the City are not functioning, it is costing each and every taxpayer dearly.

For sure, Councillors can chisel away at individual issues in their ward, and some City wide issues. To improve the internal operations, to improve the corporate culture, to improve on service delivery and to shift the bureaucracy into a mode where EVERYONE is clear on goals, objectives and priorities, and pulling in the same direction, requires STRONG LEADERSHIP at the top! It requires a Mayor and the Executive Policy Committee to set clear direction to the CAO, and to ensure the CAO is delivering on the goals set out.

Can a new CAO turn the city around and save taxpayers millions through getting the internal workings of the City – working? I am ever the optimist, but ULTIMATELY – the leadership and direction given to the CAO, is the responsibility of the Mayor and his Executive Policy Committee. Considering how the internal operations have been handled these last five years, I do have serious concerns going forward.


The City of Winnipeg Charter* states that the Mayor and the Executive Policy Committee assign the powers, duties and functions for the CAO. No one else. Again at a recent Council meeting, this was reiterated by the Mayor. The Mayor and the Executive Policy Committee are responsible for ensuring the CAO’s job performance metrics are met, and for ensuring the CAO’s overall accountability. Under the current Governance Model by which the City is governed, and the manner in which information is shared exclusively to the Mayor, the Executive Policy Committee and Deputy Mayor Delegates, the Mayor and Executive Policy Committee determine what the CAO’s priorities will be, and will give the CAO their marching orders. I wish the new CAO much luck.

*The City of Winnipeg Charter (enacted by Legislative Assembly of Manitoba) identifies the powers and reporting structure for the Chief Administrative Officer:

Section 97

The powers, duties and functions of the chief administrative officer for the city include

(a) Carrying out the powers, duties and functions assigned to the officer by this or any other Act or by council or the executive policy committee of council;

(b) Informing executive policy committee in respect of the operations and administration of the city;

(c) Ensuring that by-laws and resolutions passed by council and the city’s policies and programs are implemented;

(d) Except as council otherwise directs, managing and supervising employees;

(e) except as council otherwise directs, and subject to an employee’s contract or collective agreement or the terms of an employee’s employment, appointing, suspending or dismissing employees other than statutory officers; and

(f) Ensuring the preparation of annual operating and capital budgets.